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

HRID 2367256ノート

反応式

HRID 2367256 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-4c27407178b24a98809f3fa8e960f51e
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

反応ノート

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