Potassium Carbonate → 1-(2-aminopyrimidin-4-yl)-6-ethynyl-N,N-dimethylindazole-3-carboxamide

HRID 1398597Notes

Reaction equation

HRID 1398597 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][Si](C)(C)C)[CH:15]=3)[C:10]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[N:9]2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[CH:18])[CH:15]=3)[C:10]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[N:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 681819321-(2-aminopyrimidin-4-yl)-N,N-dimethyl-6-[2(trimethylsily)ethynyl]indazole-3-carboxamide

Product 1

HCID 866695911-(2-aminopyrimidin-4-yl)-6-ethynyl-N,N-dimethylindazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-aminopyrimidin-4-yl)-N,N-dimethyl-6-[2-(trimethylsilyl)ethynyl]indazole-3-carboxamide (250 mg, 0.66 mmol) in methanol (5 mL) and DCM (10 mL) was added K2CO3(182.57 mg, 1.32 mmol). The reaction mixture was stirred for 1 hr and then filtered by suction filtration. The precipitate was washed with DCM and methanol and the filtrate was concentrated in vacuo to give the title intermediate: 1H NMR (250 MHz, DMSO) delta 3.08 (3H, s), 3.29 (3H, br. s.), 4.42 (1H, s), 7.06 (1H, d, J=5.63 Hz), 7.14 (2H, br. s.), 7.41-7.48 (1H, m), 7.97 (1H, d, J=8.22 Hz), 8.31 (1H, d, J=5.48 Hz), 9.04 (1H, s); LC-MS: m/z=+307.00 (M+H)+.

Workup

  1. filtrationfiltered by suction filtration
  2. washThe precipitate was washed with DCM and methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5db2ffbc17a24c90b22ad85dc3b97832
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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