Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinazoline

HRID 871398ノート

反応式

HRID 871398 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178486768HCID 178486768、化合物

生成物 1

HCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline収率 72%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

A stirred mixture of 7-(benzyloxy)-6-methoxyquinazolin-4-ol (5.10 g, 18.09 mmol) and phosphorous oxychloride (10 mL, 109 mmol) in dry toluene (30 mL), was heated to 120° C. for 2 h. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with sat aqueous NaHCO3 solution (2×100 mL). The organic layer was separated and dried over MgSO4 then concentrated under reduced pressure to afford 7-(benzyloxy)-4-chloro-6-methoxyquinazoline as a cream solid (3.89 g, 72%) which was taken into the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 8.85 (s, 1H), 7.49 (m, 2H), 7.33-7.43 (m, 5H), 5.33 (s, 2H), 4.07 (s, 3H); LC-MS (ESI) m/z 301 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationthen concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2282ffb0330e4639a64339aaaafe250d
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

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