Triethylamine → HCID 86669125, compound

HRID 2400340Notes

Reaction equation

HRID 2400340 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1.C(N(CC)CC)C>CO>[C:1]([O:5][C:6](=[O:12])[NH:7][CH:8]1[CH2:11][N:10]([C:16]2[CH:17]=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 15194053-Aminoazetidine, 3-BOC protected

Product 1

HCID 86669125HCID 86669125, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of azetidin-3-yl-carbamic acid tert-butyl ester (635 mg, 3.4 mmol), 2,4-dichloropyrimidine (500 mg, 3.4 mmol) and triethylamine (0.5 ml, 3.6 mmol) in methanol (10 ml) was stirred at room temperature overnight. The mixture was concentrated and purified by column chromatography (0-40% ethyl acetate/petroleum ether) furnishing 561 mg title compound. MS: [M+H]+=283/285

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography (0-40% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-71e10210c2764182aa6a7f2eae61af13
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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