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

HRID 930798Notes

Reaction equation

HRID 930798 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.Cl.[Br:18][CH2:19][CH2:20][CH2:21][NH2:22]>C(#N)C.CN(C)C=O>[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

6

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 128607653-Bromopropan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 86676391N-(3-bromopropyl)-2,6-dichloropyrimidin-4-amineYield 36.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4,6-trichloropyrimidine (10 g, 54.5 mmol) in acetonitrile (200 mL) was added triethylamine (22.80 mL, 164 mmol) at 0° C., stirred for 5 min at r.t., and then added dropwise a solution of 3-bromopropan-1-amine hydrochloride (12 g, 68.8 mmol) in N, N-dimethylformamide (5 mL). The reaction mixture was stirred for 1 h at r.t., filtered, and concentrated. Purification via FC afforded the title compound (5.6 g).

Workup

  1. stirringThe reaction mixture was stirred for 1 h at r.t.
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via FC

Sources & evidence

ORD record
ord-506766fcf7174ea5b12ff8ae2ab85518
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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