Methanol → 5-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one

HRID 41517

반응식

HRID 41517 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([CH3:20])=[CH:15][N:14]=1.CO>O>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8](=[O:10])[NH:7][C:6]=3[CH:11]=2)[C:16]([CH3:20])=[CH:15][N:14]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 268565-Amino-2,3-dihydro-1,3-benzoxazol-2-oneHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-

생성물 1

HCID 580713875-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one수율 71%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a vial with 5-aminobenzo[d]oxazol-2(3H)-one (300.1 mg, 2.0 mmol) and 2,4-dichloro-5-methylpyrimidine (423.8 mg, 2.6 mmol), MeOH (8 mL) and H2O (2 mL) were added. The turbid mixture was stirred at room temperature for 64 h. Precipitate from reaction mixture was collected by filtration, washing with EtOAc (3 mL×2), and was further dried in vacuo. 5-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one was obtained as an off-white solid: 394 mg (71% yield); 1H NMR (300 MHz, DMSO) δ 11.68 (br s, 1H), 8.62 (s, 1H), 7.94 (d, J=0.8, 1H), 6.97 (d, J=2.0, 1H), 6.82 (d, J=8.1, 1H), 6.74 (dd, J=2.0, 8.1, 1H), 2.15 (s, 3H); LCMS (M+) m/z 277.10.

후처리

  1. customPrecipitate from reaction mixture
  2. filtrationwas collected by filtration
  3. washwashing with EtOAc (3 mL×2)
  4. customwas further dried in vacuo

출처 및 근거

ORD 기록
ord-7bf7f454a19f4f6f98ecb09d8f336a9f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530656B2

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