Sweetener compositions and methods of making them

A method of reducing the amount of sucralose in a sucralose-containing ingestible composition, comprising:

• replacing the sucralose in the sucralose-containing ingestible composition with an effective amount of sucralose and 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-one or salts, solvates and/or esters thereof, thereby forming an enhancer-containing ingestible composition;
• whereby:
• the amount of sucralose in the sucralose-containing ingestible composition is less than the amount of sucralose in the sucralose and enhancer-containing ingestible composition;
• and
• the sweetness of the sucralose-containing ingestible composition and the sucralose and enhancer-containing ingestible composition are substantially the same.

A method of improving the sweetness delivery profile of sucralose in a sucralose-containing ingestible composition, comprising:

• replacing the sucralose in the sucralose-containing ingestible composition with an effective amount of sucralose and 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-one or salts, solvates and/or esters thereof, thereby forming a sucralose and enhancer-containing ingestible composition;
• whereby:
• the sweetness of the sucralose-containing ingestible composition and the sucralose and enhancer-containing ingestible composition are substantially the same;
• and
• the sweetness onset period of the enhancer-containing ingestible composition is shorter than the sweetness onset period of the sucralose-containing ingestible composition;
• and/or
• the sweetness lingering period of the enhancer-containing ingestible composition is shorter than the sweetness lingering period of the sucralose-containing ingestible composition.

A process of preparing a compound having structural Formula (a):

• comprising:
• mixing a compound having structural Formula (b):
• with a compound having structural Formula (c):
• in the presence of an organic amine at a temperature of about 0° C. or below to obtain a reaction mixture;
• maintaining the reaction mixture at a temperature of about 0° C. or below for about 30 to about 90 minutes;
• concentrating the reaction mixture to obtain a slurry;
• and
• filtering the slurry to obtain the compound having structural Formula (a) as solid particles;
• wherein:
• R1 is hydrogen, alkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl;
• R2 is hydrogen, alkyl, heteroalkyl, alkenyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl;
• or alternatively, R1 and R2, together with the atoms to which they are attached, form a carbocyclic ring or heterocyclic ring;
• X is CN or —C(O)R3;
• R3 is alkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, OR4, or N(R42;
• and
• each R4 is independently hydrogen, alkyl, aryl, heteroaryl, arylalkyl, or heteroarylalkyl.