Diisopropylethylamine → 6-chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 1641393노트

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HRID 1641393 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[C:5](Cl)=[C:4]([Cl:16])[N:3]=1.CCN(C(C)C)C(C)C.ClC1C(NC2C=C(OC(C)C)NN=2)=NC([NH:33][C@H:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)[CH3:35])=NC=1>CCO>[Cl:16][C:4]1[N:3]=[C:2]([NH:33][C@H:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)[CH3:35])[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[CH:5]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 509937282,5,6-trichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 178458654HCID 178458654, 화합물

생성물 1

HCID 866248106-chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine수율 26.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
140 °C

실험 절차

To a solution of 2,5,6-trichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 39; 2.0 g, 8.2 mmol) in absolute EtOH (40 ml) were added DIEA (2.5 ml) and (15)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 1.2 g, 8.2 mmol) and the resulting solution was heated to 140° C. for 12 hours. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give an oil which was purified by Gilson (20-75% acetonitrile/H2O, 35 min) to give the titled compound as solid (762 mg). m/z: 383.

후처리

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe organic layer was washed with brine
  3. customdried
  4. customThe solvents were removed under reduced pressure
  5. customto give an oil which
  6. customwas purified by Gilson (20-75% acetonitrile/H2O, 35 min)

출처 및 근거

ORD 기록
ord-60338ad174ce4776906f7f7e8acd1ae2
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114989B2

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