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

HRID 1768562ノート

反応式

HRID 1768562 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c893120e79e483385480402d9fa85f3
出典データセット
uspto-grants-1995_01
特許番号
US05378708

反応ノート

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