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

HRID 2111666노트

반응식

HRID 2111666 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f1f374a4c88245bab87ffeae28d1d9ba
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521453B2

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