Potassium Carbonate → 1-(4-Amino-5-methyl-pyrimidin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

HRID 2279616Notes

Reaction equation

[C:1]12([CH2:11][NH:12][C:13]([C:15]3[C:16]([CH3:20])=[N:17][NH:18][CH:19]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][N:25]=[C:24](Cl)[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[C:16]([CH3:20])=[N:17][N:18]([C:24]4[N:23]=[C:22]([NH2:21])[C:27]([CH3:28])=[CH:26][N:25]=4)[CH:19]=3)=[O:14])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of 3-methyl-1H-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide (1.6 g, 5.85 mmol), 4-amino-2-chloro-5-methylpyrimidine (924 mg, 6.4 mmol) and potassium carbonate (1.6 g, 11.7 mmol) in DMSO (10 mL) is heated at 165° C. for 14 h. The mixture is cooled to RT and partitioned between EtOAc and water and separate the layers. The aqueous layer is extracted twice with further EtOAc. The extracts are combined, dried and evaporated. Purification by flash chromatography eluting with a mixture of 7% MeOH and 1% TEA in DCM affords the title compound.

Workup

temperatureThe mixture is cooled to RT
custompartitioned between EtOAc and water
customseparate the layers
extractionThe aqueous layer is extracted twice with further EtOAc
customdried
customevaporated
customPurification by flash chromatography
washeluting with a mixture of 7% MeOH and 1% TEA in DCM

Sources & evidence

ORD record: ord-0684e808949a44e3b403673f934c4523
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133204B2

Reaction notes

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