Diisopropylethylamine → HCID 86613131、化合物

HRID 60527ノート

反応式

HRID 60527 の反応式
[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:29][NH:30][C@@H:31]([CH2:36][OH:37])[CH2:32][CH:33]([CH3:35])[CH3:34]>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([N:30]([CH3:29])[C@H:31]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:36][OH:37])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amineHCID 59967423282525-49-9

生成物 1

HCID 86613131HCID 86613131、化合物収率 72.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (1.5 g, 4.86 mmol), DIPEA (691 mg, 5.35 mmol) and (R)—N-methylleucinol (956 mg, 7.29 mmol) were mixed in NMP (7.5 mL). The resulting solution was stirred at 110° C. under a nitrogen atmosphere for 2 days. After cooling to room temperature the reaction mixture was poured onto ice. The resulting yellow precipitate was collected by filtration, washed with water and dried in vacuo. The crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100) to give 1.42 g (72% yield) of the title compound as a yellow solid.

後処理

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. additionwas poured onto ice
  3. filtrationThe resulting yellow precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customThe crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100)

出典と根拠

ORDレコード
ord-f0a8b299aa924c8facecfbf85b09942e
出典データセット
uspto-grants-2016_09
特許番号
US09440992B2

反応ノート

読み込み中…