Dimethylformamide → 2-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde

HRID 390814ノート

反応式

HRID 390814 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([Li])CCC.CN([CH:25]=[O:26])C>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][C:9]([CH:25]=[O:26])=[CH:8][C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 568337412-Chloro-4-morpholinofuro[3,2-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 568337422-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (40 mg, 1.0 eq) dissolved in THF (1.7 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.14 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. DMF (0.05 ml, 4.0 eq) was added and reaction mixture was allowed to slowly warm up to room temperature and stirred for 90 minutes. Reaction mixture was quenched with water, and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The crude reaction mixture was purified by flash chromatography to yield 2-chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde 39 (22 mg, 50%): 1H NMR (CDCl3, 400 MHz) δ 9.92 (s, 1H), 7.48 (s, 1H), 4.12 (m, 4H), 3.86 (dd, 4H); MS (Q1) 268 (M)+.

後処理

  1. customReaction mixture
  2. customreaction mixture
  3. temperatureto slowly warm up to room temperature
  4. stirringstirred for 90 minutes
  5. customReaction mixture
  6. customwas quenched with water
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude reaction mixture
  11. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-04d25a93cad54a419b1b79589362be61
出典データセット
uspto-grants-2013_02
特許番号
US08383620B2

反応ノート

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