Diisopropylethylamine → 5-Bromo-2-(3-methylisoxazol-5-ylmethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

HRID 2111665

반응식

HRID 2111665 반응식
Cl.[NH2:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([CH3:9])[CH:5]=1.[Br:10][C:11]1[C:12]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)=[N:13][C:14](Cl)=[N:15][CH:16]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Br:10][C:11]1[C:12]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)=[N:13][C:14]([NH:2][CH2:3][C:4]2[O:8][N:7]=[C:6]([CH3:9])[CH:5]=2)=[N:15][CH:16]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 45792534(3-Methyl-1,2-oxazol-5-yl)methanamine hydrochlorideHCID 509936455-bromo-2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-4-Pyrimidinamine

생성물 1

HCID 601542855-Bromo-2-(3-methylisoxazol-5-ylmethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine수율 31%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
120 °C

실험 절차

A mixture of 5-aminomethyl-3-methylisoxazole hydrochloride (890 mg, 6.0 mmol), 5-bromo-2-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Method 1; 578 mg, 2.0 mmol) and N,N-diisopropylethylamine (1.4 ml, 8.0 mmol) in 1-butanol (10 ml) was heated at 120° C. for 18 hours. The mixture was allowed to cool to ambient temperature and volatiles removed by evaporation. The residue was triturated with ether and the product collected by filtration to give the titled compound (225 mg, 31%). 1H NMR (DMSO): δ 2.15 (s, 3H), 2.2 (s, 3H), 4.5 (m, 2H), 6.1 (br s, 2H), 7.6 (br s, 1H), 8.0 (br s, 2H), 12.05 (br s, 1H); MS: m/z 366.

후처리

  1. temperatureto cool to ambient temperature
  2. customvolatiles removed by evaporation
  3. customThe residue was triturated with ether
  4. filtrationthe product collected by filtration

출처 및 근거

ORD 기록
ord-cf5dbee485fe4d8dbb0df7bc2ba3b85d
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521453B2

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