Methanol → N-benzyl-2-chloropyrimidin-4-amine

HRID 1024393Notes

Reaction equation

HRID 1024393 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C.CO>C1COCC1.C(Cl)Cl>[CH2:9]([NH:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 1712887N-benzyl-2-chloropyrimidin-4-amineYield 54.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (0.15 g, 1.0 mmol), benzylamine (0.109 ml, 1.0 mmol) in THF was added DIPEA (0.526 ml, 3.0 mmol) and the reaction was heated at reflux for 2 hours resulting in formation of a 4:1 mixture of regioisomers (desired versus undesired) by TLC (5% Methanol:methylene chloride). The reaction was stripped down in vacuo and purified by silica column (eluent:2% methanol:methylene chloride) giving 0.12 g (0.548 mmol) of desired product 10 in 54% yield. LC/MS (M+1)=220

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 hours
  3. custompurified by silica column (eluent:2% methanol:methylene chloride)

Sources & evidence

ORD record
ord-0d0256c1cacc4b89bc05b55ef90a99e5
Source dataset
uspto-grants-2014_05
Patent number
US08722889B2

Reaction notes

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