Pentylamine → 2-Amino-4-chloro-6-(pentylamino)pyrimidine-5-carbaldehyde

HRID 1617215Notes

Reaction equation

HRID 1617215 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]=[O:10])=[C:4]([Cl:11])[N:3]=1.[CH2:12]([NH2:17])[CH2:13][CH2:14][CH2:15][CH3:16]>CO>[NH2:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]([CH:9]=[O:10])=[C:6]([NH:17][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:7]=1

Participants

4

Reactant 2

HCID 8060PentylamineHCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehyde

Product 1

HCID 866334062-Amino-4-chloro-6-(pentylamino)pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (30 g) in MeOH (600 ml) and TEA (22 ml), pentylamine (18.5 ml) was added and heated at reflux for 3 h. The solvent was removed and the residue partitioned between EtOAc and water, the organic layer was dried and the solvent evaporated. The residue was triturated with ether/isohexane to give the subtitle compound as a solid, 20.2 g.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe solvent was removed
  4. customthe residue partitioned between EtOAc and water
  5. customthe organic layer was dried
  6. customthe solvent evaporated
  7. customThe residue was triturated with ether/isohexane

Sources & evidence

ORD record
ord-138853bc7afb4b8dbaa5aea56cc4ee91
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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