2-(Furan-2-yl)ethan-1-amine → 5-Bromo-2-(2-fur-2-ylethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

HRID 2111666ノート

反応式

HRID 2111666 の反応式
[Br:1][C:2]1[C:3]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)=[N:4][C:5]([NH:8][CH2:9][C:10]2ON=[C:12]([CH3:15])[CH:11]=2)=[N:6][CH:7]=1.NCC[C:26]1[O:27]C=CC=1>C(O)CCC>[Br:1][C:2]1[C:3]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][C:11]2[O:27][CH:26]=[CH:15][CH:12]=2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 11328632-(Furan-2-yl)ethan-1-amineHCID 601542855-Bromo-2-(3-methylisoxazol-5-ylmethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

生成物 1

HCID 601543335-Bromo-2-(2-fur-2-ylethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine収率 22%

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-bromo-2-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Method 1; 290 mg, 11.0 mmol), 2-(2-aminoethyl)furan (330 mg, 3.0 mmol) and 1-butanol (5 ml) was heated at 120° C. for 5 hours. The mixture was allowed to cool to ambient temperature and the volatiles removed by evaporation. The residue was dissolved in DCM and washed with water followed by brine. The organics were separated, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, the solid product collected and purified by column chromatography on silica gel eluting with DCM/methanol (95:5) to give the titled compound (80 mg, 22%). 1H NMR (DMSO): δ 2.1 (s, 3H), 2.85 (m, 2H), 3.45 (m 2H), 6.10 (m, 1H), 6.35 (m, 1H), 6.4 (br s, 1H), 7.15 (br s, 1H), 7.5 (s, 1H), 8.0 (br s, 2H), 12.05 (br s, 1H); MS: m/z 363.

後処理

  1. temperatureto cool to ambient temperature
  2. customthe volatiles removed by evaporation
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. customThe organics were separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was triturated with ether
  9. customthe solid product collected
  10. custompurified by column chromatography on silica gel eluting with DCM/methanol (95:5)

出典と根拠

ORDレコード
ord-f1f374a4c88245bab87ffeae28d1d9ba
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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