Ammonia → 5-Chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine

반응식

Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:13][CH2:12][O:11][CH2:10]2)[C:5]([Cl:14])=[CH:4][N:3]=1.[NH3:15]>>[Cl:14][C:5]1[C:6]([O:8][CH:9]2[CH2:13][CH2:12][O:11][CH2:10]2)=[N:7][C:2]([NH2:15])=[N:3][CH:4]=1

참가 물질

반응물 2

HCID 222Ammonia

HCID 796329822,5-Dichloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidine

생성물 1

HCID 808765925-Chloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine

실험 절차

A solution of 2,5-dichloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidine (intermediate 31,100 mg, 0.425 mmol) in NH3 (7 M in MeOH, 608 μl, 4.25 mmol) was heated to 70° C. and stirred for 16 h. The reaction mixture was cooled to room temperature and concentrated. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.04 (s, 1H), 6.78 (br. s, 2H), 5.47-5.54 (m, 1H), 3.72-3.94 (m, 4H), 2.18-2.29 (m, 1H), 1.95-2.04 (m, 1H).

후처리

concentrationconcentrated
customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

출처 및 근거

ORD 기록: ord-5a4694320b5c4fb2880e8bd6f12e3bce
출처 데이터셋: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09266883B2

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