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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
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HRID 2279616 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
165 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0684e808949a44e3b403673f934c4523
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133204B2

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