Methanol → 4'-(2-Aminopyrimidin-5-yl)-5'-fluorobiphenyl-2-thiol

HRID 1524128Notes

Reaction equation

HRID 1524128 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21]CCC(OCC)=O)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.CC([O-])(C)C.[K+].CO>C1COCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[C:16]([SH:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23665647Potassium tert-butoxideHCID 90314347Ethyl 3-(4'-(2-aminopyrimidin-5-yl)-5'-fluorobiphenyl-2-ylthio)propanoate

Product 1

HCID 903131044'-(2-Aminopyrimidin-5-yl)-5'-fluorobiphenyl-2-thiolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4′-(2-aminopyrimidin-5-yl)-5′-fluorobiphenyl-2-ylthio)propanoate (6.5 g, 16 mmol) in THF (70 mL) was added t-BuOK (3.68 g, 32.8 mmol) under a N2 atmosphere. After stirring for 10 min, methanol (5 mL) was added and the resulting mixture purified by FCC to give the title compound (4.8 g, 16 mmol, 98%). MS (ESI): mass calcd. for C16H12FN3S, 297.07; m/z found, 298.1 [M+H]+.

Workup

  1. customthe resulting mixture purified by FCC

Sources & evidence

ORD record
ord-1134bc950af74af397d9135f17853c87
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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