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

HRID 458295

반응식

HRID 458295 반응식
[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

참가 물질

6

반응물 4

HCID 244Benzyl Alcohol2회HCID 947NitrogenHCID 24758Sodium hydrideHCID 53603492-Amino-6-chloropurine

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b128acacab3c4a0381b11082d87f1ad6
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189849B2

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