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

HRID 41517

反応式

HRID 41517 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7bf7f454a19f4f6f98ecb09d8f336a9f
出典データセット
uspto-grants-2013_09
特許番号
US08530656B2

関連ノート

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