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

HRID 2111665ノート

反応式

HRID 2111665 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-cf5dbee485fe4d8dbb0df7bc2ba3b85d
出典データセット
uspto-grants-2009_04
特許番号
US07521453B2

反応ノート

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