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

HRID 260051ノート

反応式

HRID 260051 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
130 °C

実験手順

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 δ5.51 (s, 2H, ARCH2), 7.35-7.54 (m, 5H, ArH), 8.05 (d, 2H, NH2, exchange with D2O), 8.92 (s, 1H, H-6); MS (EI) calcd. m/z for C11H10N4O3 246.0752, found 246.0758; Anal. (C11H10N4O3) C, H, N.

後処理

  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

出典と根拠

ORDレコード
ord-56c8a7e15e944f1ba4274f90a18caac1
出典データセット
uspto-grants-1996_06
特許番号
US05525606

反応ノート

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