Ethyl orthoformate → 7-chloro-1H-pyrido[3,2-d]pyrimidin-4-one

반응식

[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:12](OCC)(OCC)OCC>>[Cl:8][C:6]1[CH:5]=[N:4][C:3]2[C:9](=[O:10])[N:11]=[CH:12][NH:1][C:2]=2[CH:7]=1

참가 물질

반응물 2

HCID 31214Ethyl orthoformate

HCID 218200583-Amino-5-chloropyridine-2-carboxamide

생성물 1

HCID 1785182197-chloro-1H-pyrido[3,2-d]pyrimidin-4-one수율 88.5%

반응 조건

온도: 155 °C

실험 절차

A suspension of 3-amino-5-chloropicolinamide (1.1 g, 6.41 mmol) in triethyl orthoformate (15.99 mL, 96 mmol) was stirred at 155° C. for 22 hours. After cooling to RT, the yellow precipitate was collected by vacuum filtration and washed with hexanes to yield the title intermediate (1.03 g, 5.67 mmol) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.20 (s, 1H) 8.27 (d, J=2.35 Hz, 1H) 8.80 (d, J=2.25 Hz, 1H) 12.68 (br. s., 1H). LC/MS (ESI m/z=182 (M+H).

후처리

temperatureAfter cooling to RT
filtrationthe yellow precipitate was collected by vacuum filtration
washwashed with hexanes

출처 및 근거

ORD 기록: ord-71fd9f0557964f24b2c7447445508694
출처 데이터셋: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09309263B2

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