Triethylamine → N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.C(N(CC)CC)C.Br.[Br:18][CH2:19][CH2:20][CH2:21][NH2:22]>C(#N)C>[Br:18][CH2:19][CH2:20][CH2:21][NH:22][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([Cl:1])[N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,4,6-trichloropyrimidine (100 g, 545 mmol) in acetonitrile (2000 mL) was added triethylamine (166 g, 1636 mmol) at 0° C., The reaction mixture was stirred for 5 min at rt, then 3-bromopropan-1-amine hydrobromide (119 g, 545 mmol) was added portionwise. The reaction mixture was stirred for 1 h at rt, and filtered to provide a clear solution. Purification via FC afforded the title compound as a white solid (47 g, 30% yield).
Workup
- stirringThe reaction mixture was stirred for 1 h at rt
- filtrationfiltered
- customto provide a clear solution
- customPurification via FC
Sources & evidence
- ORD record
- ord-4e833e5c2c734f7eafcbd68c19c51199
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273054B2
Reaction notes
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