Isopropylamine → Iprymidam

HRID 2367184Notes

Reaction equation

HRID 2367184 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11]>CO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:13][CH:10]([CH3:12])[CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 4867467IprymidamYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 25 mL sealable tube under argon were combined 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol) and isopropylamine (0.78 mL, 9.15 mmol) in CH3OH (15 mL). The vial was sealed and the resulting mixture was stirred overnight at 50° C. The reaction was cooled to room temperature and stirred over the weekend. The reaction mixture was concentrated, and the resulting orange oil was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to afford the title compound (453 mg, 71%) as a yellow foam. LC-MS (ES) m/z=187 [M+H]+.

Workup

  1. customIn a 25 mL sealable tube under argon were combined
  2. customThe vial was sealed
  3. temperatureThe reaction was cooled to room temperature
  4. stirringstirred over the weekend
  5. concentrationThe reaction mixture was concentrated
  6. customthe resulting orange oil was partitioned between EtOAc and water
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ee17870b9cd64398a5913583095e4786
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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