Triethylamine → (+/-)-[trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine

HRID 1243227Notes

Reaction equation

HRID 1243227 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C(N(CC)CC)C.[C:26]([Si:30]([CH3:39])([CH3:38])[O:31][C@H:32]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]>C(O)CCC>[C:26]([Si:30]([CH3:39])([CH3:38])[O:31][C@H:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:6]2[C:5]([CH2:9][NH:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=3)=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11426039(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amineHCID 58715071(+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

Product 1

HCID 86594647(+/-)-[trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine (200 mg, 0.71 mmol) (from Example 38c supra) was dissolved in hot n-butanol (2 mL) (Aldrich). After cooling to room temperature, triethylamine (0.20 mL, 0.92 mmol) (Allied Signal) and (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine (198 mg, 0.91 mmol) (from Example 9c supra) were successively added and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and purified by flash chromatography (20% ethyl acetate in hexanes) to give (±)-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-{2-chloro-5-[(4-ethyl-phenylamino)-methyl]-pyrimidin-4-yl}-amine as a viscous oil. (Yield 272 mg, 84%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b750569661fd4a9cb7e78d37530d5c96
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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