2-Chloropyrimidine → tert-Butyl 2-((pyrimidin-2-ylamino)methyl)piperidine-1-carboxylate

HRID 18080

Reaction equation

HRID 18080 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 744042-ChloropyrimidineHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 71631688tert-Butyl 2-((pyrimidin-2-ylamino)methyl)piperidine-1-carboxylate

Conditions

Temperature
100 °C

Procedure

A mixture of (RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester (1.28 g) and 2-chloropyrimidine was heated at 100° C. for 48 hours. After cooling to room temperature the mixture was column chromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant) to give the title compound (0.42 g) as an oil.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customchromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant)

Sources & evidence

ORD record
ord-11bc6b9d360c42b7badcc2370c78ce4d
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Linked notes

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