THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID,5-AMINO-4-(3-METHOXYPHENYL)-2-(METHYLTHIO)-(WXG01920) synthesis

4synthesis methods

Product Name:THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID,5-AMINO-4-(3-METHOXYPHENYL)-2-(METHYLTHIO)-(WXG01920)
CAS Number:301847-46-1
Molecular formula:C15H13N3O3S2
Molecular Weight:347.41

THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID,5-AMINO-4-(3-METHOXYPHENYL)-2-(METHYLTHIO)-,ETHYL ESTER(WXG01919)

301846-06-0
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THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID,5-AMINO-4-(3-METHOXYPHENYL)-2-(METHYLTHIO)-(WXG01920)

301847-46-1
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Yield:-

Reaction Conditions:

with lithium hydroxide in 1,4-dioxane;water at 80; for 48 h;

Steps:

1.d (d). 5-Amino-4-(3-methoxyphenyl-2-methylthio-thieno[2,3-d]pyrimidine-6-carboxylic acid

Ethyl 5-amino-4-(3-methoxyphenyl)-2-methylthio-thieno[2,3-d]pyrimidine-6-carboxylate (example 1c, 9.27 g) was dissolved in a mixture of 1,4-dioxane (270 ml) and H2O (30 ml). Lithium hydroxide (10 g) was added and the mixture was stirred at 80° C. for 48 h. 1,4-Dioxane was removed from the mixture by evaporation and the residue was taken up in H2O. The remaining solution was acidified to pH 2 by adding aq. 3N aq. HCl. The resulting precipitate was filtered off and washed with H2O. Traces of water in the precipitate were removed by coevaporation with 1,4-dioxane and then with diethylether and drying in vacuo at 50° C. overnight. Yield: 8.45 g MS-ESI: [M + H]+ = 348.0 TLC: Rf = 0.2, silica gel, CH2Cl2/CH3OH = 9/1 (v/v).

References:

US2003/225113,2003,A1 Location in patent:Page 12

5-PYRIMIDINECARBONITRILE,1,6-DIHYDRO-4-(3-METHOXYPHENYL)-2-(METHYLTHIO)-6-OXO-(WXG01917)

128640-73-3
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301847-46-1
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References

5-PYRIMIDINECARBONITRILE,4-CHLORO-6-(3-METHOXYPHENYL)-2-(METHYLTHIO)-(WXG01918)

128666-82-0
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301847-46-1
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References

591-31-1
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References