Triethylamine → N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amine

HRID 920360Notes

Reaction equation

HRID 920360 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]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 86676391N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amineYield 30.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. stirringThe reaction mixture was stirred for 1 h at rt
  2. filtrationfiltered
  3. customto provide a clear solution
  4. customPurification via FC

Sources & evidence

ORD record
ord-4e833e5c2c734f7eafcbd68c19c51199
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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