Benzyl Alcohol → 2-Amino-4-benzyloxy-5-nitropyrimidine

HRID 380339노트

반응식

HRID 380339 반응식
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[Na].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[NH2:1][C:2]1[N:7]=[C:6]([O:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

참가 물질

4

반응물 3

HCID 244Benzyl AlcoholHCID 3199954-chloro-5-nitropyrimidin-2-amineHCID 5360545Sodium

생성물 1

HCID 102639222-Amino-4-benzyloxy-5-nitropyrimidine

반응 조건

온도
130 °C

실험 절차

2-Amino-4-chloro-5-nitropyrimidine (0.70 g, 4.0 mmol) was added to a solution of sodium (0.12 g, 5.2 mmol) in benzyl alcohol (8 mL) under argon. The solution was heated in a 130° C. oil bath for 3 h, and approximately half of the benzyl alcohol was evaporated under reduced pressure. The residue was poured into water (50 mL) with constant stirring for 10 min. After neutralization with glacial acetic acid, a brown precipitate formed which was collected by filtration and washed with water. This solid was crystallized from benzene to give 5a as a golden crystalline solid: yield, 126 mg (13%); mp 164-167° C.; UV (pH 1) λmax 262 nm (ε=0.879×104), 295 (sh) (0.571×104); (pH 6.9) 235 (sh) (0.448×104), 273 (0.360×104), 326 (1.085×104); (pH 13) 273 (0.404×104), 327 (1.055×104); 1H NMR δ 5.51 (s, 2 H, ArCH2), 7.35-7.54 (m, 5 H, ArH), 8.05 (d, 2 H, NH2, exchange with D2O), 8.92 (s, 1 H, H-6); MS (EI) calcd. m/z for C11H10 N4O3 246.0752, found 246.0758; Anal. (C11H10N4O3) C, H, N.

후처리

  1. customapproximately half of the benzyl alcohol was evaporated under reduced pressure
  2. additionThe residue was poured into water (50 mL)
  3. customAfter neutralization with glacial acetic acid, a brown precipitate formed which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customThis solid was crystallized from benzene

출처 및 근거

ORD 기록
ord-380d49c5623e4ea186235c1188191c26
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303604B1

반응 노트

불러오는 중…