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Ethyl chloroformate → Ethyl-4-chloro-5-(4-(ethoxycarbonyloxy)but-1-ynyl)-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7h-pyrrolo[2,3-d]pyrimidin-2-ylcarbamate

HRID 417875
ノート
印刷プレビュー

反応式

HRID 417875 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([Cl:27])[C:5]2[C:10]([C:11]#[C:12][CH2:13][CH2:14][OH:15])=[CH:9][N:8]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:6]=2[N:7]=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>N1C=CC=CC=1.C(Cl)Cl>[CH2:32]([O:31][C:29](=[O:30])[NH:1][C:2]1[N:3]=[C:4]([Cl:27])[C:5]2[C:10]([C:11]#[C:12][CH2:13][CH2:14][O:15][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:9][N:8]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:6]=2[N:7]=1)[CH3:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10928Ethyl chloroformate2 回HCID 119505104-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol

生成物 1

HCID 57713843Ethyl-4-chloro-5-(4-(ethoxycarbonyloxy)but-1-ynyl)-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7h-pyrrolo[2,3-d]pyrimidin-2-ylcarbamate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6344
Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

A suspension of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (0.73 g) in anhydrous pyridine (5 mL) and DCM (25 mL) was treated with ethyl chloroformate (1 mL) at rt for 30 min. The mixture was cooled to 0° C., treated with addition EtOCOCl (1 mL), and the temperature was allowed to slowly reach rt overnight. The reaction mixture was diluted with DCM (30 mL) and washed sequentially with H2O, NH4OH 1M, and brine. The DCM was evaporated, but not the residual pyridine, Addition of MeOH (20 mL) induced crystallization of the product, as white needles. HPLC Rt=6.28 min.

後処理

  1. customwas allowed to slowly reach rt overnight
  2. washwashed sequentially with H2O, NH4OH 1M, and brine
  3. customThe DCM was evaporated
  4. additionnot the residual pyridine, Addition of MeOH (20 mL)
  5. customcrystallization of the product

出典と根拠

ORDレコード
ord-0a69bccd11e94f5c8a5292ed367fca31
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093229B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート