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

HRID 79104

Reaction equation

HRID 79104 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-25e649a3c96d4e73859938eb1edb6a41
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Linked notes

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