Phosphorus oxychloride → Ethyl 6-chloro-5-methylpyrimidine-4-carboxylate

반응식

O[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13]

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 178470300HCID 178470300, 화합물

생성물 1

HCID 56592992Ethyl 6-chloro-5-methylpyrimidine-4-carboxylate

반응 조건

온도: 100 °C

실험 절차

A solution of ethyl 6-hydroxy-5-methylpyrimidine-4-carboxylate 40 (100 g, 549 mmol) in POCl3 (1000 ml) was heated to reflux for 5 h at 100° C. in sealed tube. After cooling to RT, the excess POCl3 was removed under reduced pressure, then quenched with ice water and extracted with EtOAc. The combined organic phase is washed with water, brine and concentrated under reduced pressure to afford ethyl 6-chloro-5-methylpyrimidine-4-carboxylate 41 as a black liquid. Yield: 80 (72%). This material was used as such for next step without purification.

후처리

temperatureAfter cooling to RT
customthe excess POCl3 was removed under reduced pressure
customquenched with ice water
extractionextracted with EtOAc
washThe combined organic phase is washed with water, brine
concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록: ord-a6f644e9afd3433c80f6bda4a43b289e
출처 데이터셋: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09163020B2

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