Triethylamine → trans-2-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-cyclohexanol

HRID 272638Notes

Reaction equation

HRID 272638 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl.[NH2:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]1[OH:25]>C(#N)C>[Br:1][C:2]1[C:3]([NH:18][C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[OH:25])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 87694143trans-2-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-cyclohexanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An ice-cooled solution of 2.28 g (10.0 mmol) of 5-Bromo-2,4-dichloropyrimidine and 3.4 ml (24.0 mmol) of triethylamine in 10 ml of acetonitrile is mixed with 1.82 g (12.1 mmol) of trans-2-aminocyclohexanol hydrochloride. After 16 hours at room temperature the batch is filtrated and the filtrate is concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate: 1:1). 1.61 g (5.3 mmol, corresponding to 53% of theory) of the product is obtained.

Workup

  1. filtrationAfter 16 hours at room temperature the batch is filtrated
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe remaining residue is purified by chromatography (hexane/ethyl acetate: 1:1)
  4. custom1.61 g (5.3 mmol, corresponding to 53% of theory) of the product is obtained

Sources & evidence

ORD record
ord-2d6e1f60cf1947a9bcb911090491f438
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Reaction notes

Loading…