Phosphorus oxychloride → 4-Chloro-7-methoxy-quinazoline

반응식

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](O)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[CH:9][N:8]=1

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 178487763HCID 178487763, 화합물

생성물 1

HCID 189250784-Chloro-7-methoxy-quinazoline수율 99.1%

실험 절차

Step 2 A suspension of 7-methoxyquinazolin-4-ol (400 mg, 2.271 mmol) in phosphorus oxychloride (7 mL, 75 mmol) was heated at reflux for 3 h. The solution was concentrated and the residue was suspended in EtOAc and stirred on an ice bath with NaHCO3 (aq) until all the solid was dissolved and gas evolution ceased. The layers were separated and the organic phase was dried and concentrated to provide 4-chloro-7-methoxyquinazoline as a light yellow-tan solid (438 mg, 99%). 1H NMR (400 MHz, chloroform-d) δ 8.94 (1 H, s), 8.15 (1 H, d, J=9.7 Hz), 7.29-7.37 (2 H, m), 4.00 (3 H, s).

후처리

temperaturewas heated
temperatureat reflux for 3 h
concentrationThe solution was concentrated
dissolutionwas dissolved
customThe layers were separated
customthe organic phase was dried
concentrationconcentrated

출처 및 근거

ORD 기록: ord-6e27e0dba65e41c788ae4ac3843e316e
출처 데이터셋: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08362065B2

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