Benzyl Alcohol → 6-(Phenylmethoxy)-9H-purin-2-amine

HRID 458295

反応式

HRID 458295 の反応式
[H-].[Na+].N#N.[CH2:5]([OH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:14]1[N:22]=[C:21]([NH2:23])[N:20]=[C:19]2[C:15]=1[NH:16][CH:17]=[N:18]2>C1(C)C=CC=CC=1>[CH2:5]([O:12][C:14]1[N:22]=[C:21]([NH2:23])[N:20]=[C:19]2[C:15]=1[NH:16][CH:17]=[N:18]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 244Benzyl Alcohol2 回HCID 947NitrogenHCID 24758Sodium hydrideHCID 53603492-Amino-6-chloropurine

生成物 1

HCID 45786-(Phenylmethoxy)-9H-purin-2-amine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
115 °C

実験手順

60% Sodium hydride in mineral oil (2.36 g, 0.059 moles) was charged to a 500 mL 3-neck flask equipped with magnetic stirring, temperature probe, condenser, and N2 inlet. Toluene (250 mL) was added. Benzyl alcohol (50 mL) was added dropwise over 30 minutes. After addition of benzyl alcohol, the reaction was stirred 10 minutes. Then 6-chloro-2-aminopurine (5.00 g, 0.029 moles) was added and the reaction mixture was heated to reflux (115° C.) for 4.5 hours. The reaction mixture was filtered hot through a coarse glass fritted funnel and 11.65 g of wet off-white solids were obtained. The wet solids were triturated with CH2Cl2 (100 mL) and water (100 mL). After 10 minutes of stirring the solids had dissolved. The aqueous layer was separated and the pH was lowered to 9 over 3 minutes with 6 M HCl. A white solid precipitate formed. The slurry was filtered, washed with water (50 mL), and dried (in vacuo at 50° C.) to a constant weight to provide the desired product as off-white crystals (5.15 g).

後処理

  1. temperaturethe reaction mixture was heated
  2. filtrationThe reaction mixture was filtered hot through a coarse glass fritted funnel

出典と根拠

ORDレコード
ord-b128acacab3c4a0381b11082d87f1ad6
出典データセット
uspto-grants-2007_03
特許番号
US07189849B2

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