Ammonium hydroxide isopropanol → 5-Bromo-N4-cyclopentylpyrimidine-2,4-diamine

HRID 875936

Reaction equation

HRID 875936 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH4+:15].[OH-].C(O)(C)C>>[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:15])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 22611478Ammonium hydroxide isopropanolHCID 442482475-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine

Product 1

HCID 582998155-Bromo-N4-cyclopentylpyrimidine-2,4-diamineYield 66%

Procedure

A solution of 1 (45 g, 200 mmol) in 28% NH4OH/iso-propanol (1/1, 400 mL) was heated at 120° C. in a sealed tube for 22 h. The product was extracted with dichloromethane and the organic layers were washed with brine and dried. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in hexanes to give the titled compound (2) as a white solid (34 g, 66%). 1H NMR (500 MHz, DMSO-d6) δ 7.77 (1H, s), 6.19 (2H, br. s), 6.12 (1H, d, 1H, J=7.3 Hz), 4.33 (1H, m) 1.90 (2H, m), 1.69 (2H, m), 1.49-1.55 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 257.0, Calculated 257.0.

Workup

  1. extractionThe product was extracted with dichloromethane
  2. washthe organic layers were washed with brine
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a3030d30d7414eef8d97965731f19afb
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Linked notes

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