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

HRID 1617194Notes

Reaction equation

HRID 1617194 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

A mixture of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (30 g), pentylamine (18.5 ml) and TEA (22 ml) in MeOH (600 ml) were heated under reflux for 3 h then partitioned between EtOAc/water. The organics were separated, washed with water, dried and evaporated under reduced pressure. The residue was triturated with ether/iso-hexane to afford the subtitle compound, 20 g.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 3 h
  3. customthen partitioned between EtOAc/water
  4. customThe organics were separated
  5. washwashed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ether/iso-hexane

Sources & evidence

ORD record
ord-8d28d53c12d541aab57f4b6a78a65035
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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