Potassium Carbonate → 5-ethynyl-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

HRID 1042743Notes

Reaction equation

HRID 1042743 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14]#[C:15][Si](C)(C)C)=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:14]([C:6]1[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:8][C:3]([NH:2][CH3:1])=[N:4][CH:5]=1)#[CH:15]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68459491N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine

Product 1

HCID 593743985-ethynyl-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25 mL round bottom flask was charged with N-methyl-4-(thiophen-2-yl)-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine (0.518 g, 1.80 mmol), methanol (20 mL), and potassium carbonate (0.747 g, 5.41 mmol), and the reaction mixture stirred at room temperature for 24 hours. The reaction mixture was concentrated and the residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to 5-ethynyl-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine. MS m/z=216 [M+H]+. Calc'd for C11H9N3S: 215.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified via column chromatography on silica gel (gradient elution with 0-100% ethyl acetate-hexane) to 5-ethynyl-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

Sources & evidence

ORD record
ord-170ef827e81d4d2db0264c1f493c50aa
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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