Dimethylformamide → 2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide

HRID 595051노트

반응식

HRID 595051 반응식
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][S:9](=[O:12])(=[O:11])[CH2:8][C:6]=2[N:7]=1.CC[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18].CN([CH:24]=[O:25])C>>[Cl:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:17][CH2:18][O:25][CH2:24][C@@H:19]2[CH3:20])[C:5]2[CH2:10][S:9](=[O:12])(=[O:11])[CH2:8][C:6]=2[N:7]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 894874532,4-dichloro-5H,7H-6lambda6-thieno(3,4-d)pyrimidine-6,6-dione

생성물 1

HCID 894946042-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide수율 66%

실험 절차

To a solution of 2,4-dichloro-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (120 mg, 0.5 mmol) and Et3N (101 mg, 1.0 mmol) in DMF (5.0 mL) at 0° C. was added a mixture of(S)-3-methylmorpholine (51 mg, 0.5 mmol) dropwise. After the addition was complete, the mixture was stirred overnight at rt. The solvent was removed under vacuum to give a residue which was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and concentrated to give the product which was purified by preparative TLC (Eluent: petroleum ether/ethyl acetate=2/1) to provide 2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide as a light yellow solid (100 mg, 66%).

후처리

  1. additionAfter the addition
  2. customThe solvent was removed under vacuum
  3. customto give a residue which
  4. customwas partitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give the product which
  9. customwas purified by preparative TLC (Eluent: petroleum ether/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-00f2d6bc9d604180abfe70732f6a3d27
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242993B2

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