Diethyl Ether → 5-chloro-6-ethyl-N-[1-[4-(trimethylsilyl)phenyl]ethyl]-4-pyrimidinamine

HRID 1768562노트

반응식

HRID 1768562 반응식
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)[NH2:3].Cl[C:15]1[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[N:18]=[CH:17][N:16]=1.C(N(CC)CC)C.CCOCC>C1(C)C=CC=CC=1.O>[Cl:21][C:20]1[C:15]([NH:3][CH:2]([C:4]2[CH:9]=[CH:8][C:7]([Si:10]([CH3:12])([CH3:11])[CH3:13])=[CH:6][CH:5]=2)[CH3:1])=[N:16][CH:17]=[N:18][C:19]=1[CH2:22][CH3:23]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 18948843alpha-Methyl-4-trimethylsilylbenzenemethanamine

생성물 1

HCID 189488445-chloro-6-ethyl-N-[1-[4-(trimethylsilyl)phenyl]ethyl]-4-pyrimidinamine수율 60%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

The product of Step D (17 g, 86 mole), 4,5-dichloro-6-ethylpyrimidine (15 g, 86 mole) and triethylamine (24 mL, 170 mole) were dissolved in toluene (65 mL). The reaction mixture was heated to reflux overnight and then cooled. Ether and water were added and the mixture was partitioned. The aqueous phase was extracted two times with ether and the combined organic phases were dried (MgSO4) and concentrated. The resultant solid was recrystallized from acetonitrile to give the title compound as a white solid (17 g, 60% yield), mp 79°-80° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. customthe mixture was partitioned
  5. extractionThe aqueous phase was extracted two times with ether
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe resultant solid was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-1c893120e79e483385480402d9fa85f3
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378708

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