3-Amino-5-methyl-thiophene-2-carboxylic acid methyl ester → 5-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester

HRID 570501Notes

Reaction equation

HRID 570501 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[C:12]2[CH:19]=[CH:18][NH:17][C:13]=2[N:14]=[CH:15][N:16]=1)=[O:4].N[C:21]1C=C(C)SC=1C(OC)=O>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:21])=[CH:8][C:9]=1[NH:10][C:11]1[C:12]2[CH:19]=[CH:18][NH:17][C:13]=2[N:14]=[CH:15][N:16]=1)=[O:4]

Participants

3

Reactant 2

HCID 8189523-Amino-5-methyl-thiophene-2-carboxylic acid methyl esterHCID 669578463-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 669577805-Methyl-3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl esterYield 45%

Procedure

The title compound was prepared in an analogous manner as 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methyl ester using methyl 3-amino-5-methylthiophene-2-carboxylate instead of methyl 3-amino-2-thiophenecarboxylate and obtained in 45% yield (HPLC: 99%, RT: 6.89 min). 1H NMR (DMSO-d6) 12.40 (br s, 1H), 10.58 (br s, 1H), 8.44 (s, 1H), 7.96 (br s, 1H), 7.47 (dd, J=3.1, 2.6 Hz, 1H), 6.63 (dd, J=3.3, 1.5 Hz, 1H), 3.82 (s, 3H), 2.55 (s, 3H); MS (m/z) 289 [M+H]+.

Workup

  1. customobtained in 45% yield (HPLC: 99%, RT: 6.89 min)

Sources & evidence

ORD record
ord-4b285fdf43f5487485993cb6de4f2361
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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