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

HRID 1777875Notes

Reaction equation

HRID 1777875 reaction equation
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

Participants

3

Reactant 2

HCID 222AmmoniaHCID 796329822,5-Dichloro-4-((tetrahydrofuran-3-yl)oxy)pyrimidine

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-5a4694320b5c4fb2880e8bd6f12e3bce
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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