Triethylamine → HCID 58504685, compound

HRID 2367192Notes

Reaction equation

HRID 2367192 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH:10]1[CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>CO>[N:10]1([C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10422AzetidineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 58504685HCID 58504685, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 25 mL sealable tube were combined 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol), azetidine (0.21 mL, 3.05 mmol), and triethylamine (1.06 mL, 7.62 mmol) in CH3OH (10 mL). The vial was sealed and the reaction mixture was stirred overnight at 50° C. The reaction was concentrated and the resulting solid was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (314 mg, 53%) as a yellow solid. LC-MS (ES) m/z=185 [M+H]+.

Workup

  1. customIn a 25 mL sealable tube were combined
  2. customThe vial was sealed
  3. concentrationThe reaction was concentrated
  4. customthe resulting solid was partitioned between EtOAc and water
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9bf31688ee4e4628a088deac1fd27f47
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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