Cyclohexylamine → HCID 21433275, compound

HRID 2367190Notes

Reaction equation

HRID 2367190 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 21433275HCID 21433275, compoundYield 108.5%

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 cyclohexylamine (0.87 mL, 7.62 mmol) and CH3OH (10 mL). The vial was sealed, and the reaction mixture was stirred for 2 days at 50° C. The reaction was cooled to room temperature and concentrated. The resulting 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 (750 mg, 99%) as an orange oil. LC-MS (ES) m/z=227 [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. concentrationconcentrated
  5. customThe resulting oil was partitioned between EtOAc and water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ef1026474fd84133bd6ad1cbc16cea5d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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