Ethyl 2-aminothiophene-3-carboxylate → 3-hydroxy-1H-thieno[2,3-d]pyrimidine-2,4-dione

HRID 550709Notes

Reaction equation

HRID 550709 reaction equation
C(OC(C1C=CSC=1N)=O)C.COC1C=C(OC)C=CC=1C[O:17][N:18]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][S:27][C:21]=2[NH:20][C:19]1=[O:28]>>[OH:17][N:18]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][S:27][C:21]=2[NH:20][C:19]1=[O:28]

Participants

3

Reactant 2

HCID 1988156Ethyl 2-aminothiophene-3-carboxylateHCID 672022653-(2,4-Dimethoxy-benzyloxy)-1H-thieno[2,3-d]pyrimidine-2,4-dione

Product 1

HCID 3150233-hydroxy-1H-thieno[2,3-d]pyrimidine-2,4-dione

Procedure

2-Amino-thiophene-3-carboxylic acid ethyl ester was transformed to the O-protected intermediate 3-(2,4-Dimethoxy-benzyloxy)-1H-thieno[2,3-d]pyrimidine-2,4-dione using general procedure A1. Deprotection of this intermediate using general procedure D1 gave the title compound which was purified by mass triggered preparative HPLC. 1H NMR (DMSO-d6) δ 10.39 (bs, 1H), 7.16 (d, 1H, J=5.7 Hz), 7.12 (d, 1H, J=5.7 Hz); Electrospray MS: 183 (M−H); retention time: 1.25 min.

Sources & evidence

ORD record
ord-7ffe72b812984631b3a86e35e1576603
Source dataset
uspto-grants-2011_05
Patent number
US07947691B2

Reaction notes

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