Sodium → HCID 178448297、化合物

HRID 1694550ノート

反応式

HRID 1694550 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:17])[C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:18]CC3C=CC=CC=3)=[N:6][C:5]=2[N:26]=1.[Na]>N>[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:17])[C@H:11]([CH2:14][CH2:15][CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:26]=1

参加物

4

反応物 2

HCID 5360545SodiumHCID 59868836(2R)-2-{[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl](methyl)amino}pentan-1-ol

生成物 1

HCID 178448297HCID 178448297、化合物収率 81.2%

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

反応条件

温度
-33 °C

実験手順

A round-bottomed flask was equipped with a dry ice-ethanol condenser and immersed in a dry ice-ethanol cooling bath. Ammonia (200 mL) was condensed into the flask followed by the addition of (2R)-2-{[2-amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl](methyl)amino}pentan-1-ol (5.43 g, 13.9 mmol). The resulting mixture was allowed to warm to −33° C. and sodium metal was added in small pieces until a blue colour appeared and persisted for 30 seconds. The reaction was then quenched by addition of a spoon of solid ammonium chloride. The ammonia was evaporated off and water (250 mL) was added to the residue. The resulting mixture was neutralized with 1M hydrochloric acid (aq.). The precipitated product was collected by filtration, washed with water and acetonitrile and dried in vacuo to yield 3.38 g (81% yield) of the title compound.

後処理

  1. customA round-bottomed flask was equipped with a dry ice-ethanol condenser
  2. customimmersed in a dry ice-ethanol cooling bath
  3. customcondensed into the flask
  4. customThe reaction was then quenched by addition of a spoon of solid ammonium chloride
  5. customThe ammonia was evaporated off
  6. additionwater (250 mL) was added to the residue
  7. filtrationThe precipitated product was collected by filtration
  8. washwashed with water and acetonitrile
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-4b30f871ac214c65b29c0f57519551a3
出典データセット
uspto-grants-2012_04
特許番号
US08158785B2

反応ノート

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