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

HRID 595051Notes

Reaction equation

HRID 595051 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-00f2d6bc9d604180abfe70732f6a3d27
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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