Azepane → HCID 31537603, compound

HRID 2367220Notes

Reaction equation

HRID 2367220 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>CO>[Cl:8][C:6]1[CH:7]=[C:2]([N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=[C:4]([NH2:9])[N:5]=1

Participants

5

Reactant 3

HCID 8119AzepaneHCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 31537603HCID 31537603, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 25 mL sealable tube under nitrogen were combined 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol) and hexahydro-1H-azepine (0.34 mL, 3.05 mmol) in CH3OH (10 mL). Triethylamine (0.47 mL, 3.35 mmol) was added, the vial was sealed, and the reaction mixture was stirred for 5 hours at 50° C. The reaction was cooled to room temperature and concentrated. The resulting yellow solid was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (600 mg, 82%) as a yellow solid. LC-MS (ES) m/z=227 [M+H]+.

Workup

  1. customIn a 25 mL sealable tube under nitrogen were combined
  2. customthe vial was sealed
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. customThe resulting yellow solid was partitioned between EtOAc and water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9a5329a34f9746299b5abde49059f7ca
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…