Triethylamine → 6-chloro-N4-[1-(phenylmethyl)cyclopropyl]-2,4-pyrimidinediamine

HRID 2367256Notes

Reaction equation

HRID 2367256 reaction equation
Cl.[C:2]1([CH2:8][C:9]2([NH2:12])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([NH2:21])[N:15]=1.CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>C(O)C>[Cl:13][C:14]1[N:15]=[C:16]([NH2:21])[N:17]=[C:18]([NH:12][C:9]2([CH2:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:11][CH2:10]2)[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 242065861-Benzylcyclopropan-1-amine hydrochloride

Product 1

HCID 866591746-chloro-N4-[1-(phenylmethyl)cyclopropyl]-2,4-pyrimidinediamineYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-(phenylmethyl)cyclopropanamine_hydrochloride (530 mg, 2.88 mmol), 4,6-dichloro-2-pyrimidinamine (295 mg, 1.80 mmol), Et3N (911 mg, 9 mmol) and K2CO3 (249 mg, 1.80 mmol) in ethanol (6 mL) was stirred and heated at 140° C. for 4 hours in a Biotage Initiator microwave synthesizer. The mixture was cooled to room temperature and concentrated to dryness. The resulting solids were partitioned between EtOAc and water. The organic layer was separated, dried (Na2SO4), concentrated to dryness and purified by reverse phase chromatography using CH3CN in water from 32% to 42% (0.05% trifluoroacetic acid in water) in 8 min to afford the title compound (204 mg) as a white solid. LC-MS (ES) m/z=275 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe resulting solids were partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. custompurified by reverse phase chromatography
  8. customin 8 min

Sources & evidence

ORD record
ord-4c27407178b24a98809f3fa8e960f51e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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