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

HRID 2279616
Notes
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Reaction equation

HRID 2279616 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 178434554HCID 178434554, compound

Product 1

HCID 252248521-(4-Amino-5-methyl-pyrimidin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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

  1. temperatureThe mixture is cooled to RT
  2. custompartitioned between EtOAc and water
  3. customseparate the layers
  4. extractionThe aqueous layer is extracted twice with further EtOAc
  5. customdried
  6. customevaporated
  7. customPurification by flash chromatography
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes