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

HRID 390814노트

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HRID 390814 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-04d25a93cad54a419b1b79589362be61
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383620B2

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