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2-Amino-4,6-dichloropyrimidine → 6-Chloro-N4-(1,1-dimethyl-2-phenylethyl)-2,4-pyrimidinediamine

HRID 2367260
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HRID 2367260 반응식
Cl.[CH3:2][C:3]([NH2:12])([CH3:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16]([NH2:21])[N:15]=1.CCN(C(C)C)C(C)C>CC#N>[Cl:13][C:14]1[N:15]=[C:16]([NH2:21])[N:17]=[C:18]([NH:12][C:3]([CH3:2])([CH3:11])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:19]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 70969Phentermine HydrochlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 866591756-Chloro-N4-(1,1-dimethyl-2-phenylethyl)-2,4-pyrimidinediamine수율 50.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
160 °C

실험 절차

A mixture of 2-methyl-1-phenyl-2-propanamine hydrochloride (742 mg, 4 mmol), 4,6-dichloro-2-pyrimidinamine (438 mg, 2.67 mmol) and Hunig's base (1.55 g, 12 mmol) in CH3CN (8 mL) was stirred and heated for 6 hours at 160° C. 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, and the organic layer was dried over Na2SO4, filtered and concentrated to dryness. Purification by reverse phase chromatography using CH3CN in water from 45% to 65% (0.08% ammonium hydrogen carbonate) in 18 min, afforded the title compound (373 mg) as a white solid. LC-MS (ES) m/z=277.0 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe resulting solids were partitioned between EtOAc and water
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification by reverse phase chromatography
  8. customin 18 min

출처 및 근거

ORD 기록
ord-4c89eb78c272415e85a7dc478c89c68c
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697685B2

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