Triethylamine → HCID 89487442, compound

HRID 595076Notes

Reaction equation

HRID 595076 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][S:9](=[O:12])(=[O:11])[CH:8]([CH3:13])[C:6]=2[N:7]=1.C(N(CC)CC)C.[CH3:22][C@H:23]1[CH2:28][O:27][CH2:26][CH2:25][NH:24]1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][C@@H:23]2[CH3:22])[C:5]2[CH2:10][S:9](=[O:12])(=[O:11])[CH:8]([CH3:13])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 894873191429639-82-6

Product 1

HCID 89487442HCID 89487442, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-7-methyl-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (Example 7, step (vi)) (160 mg, 0.63 mmol), and triethylamine (64 mg, 0.63 mmol) in DMF (3 mL) at 0° C. was added 3-(S)-methylmorpholine (57 mg, 0.57 mmol). The resultant mixture was stirred at rt for 2 h. The solvent was removed under vacuum and the residue obtained partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to give the product which was purified by preparative TLC (petroleum ether/ethyl acetate=2/1) to produce 2-chloro-7-methyl-4-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (72 mg, 36% yield). LC-MS (Method A), (ES+) 318/320, RT=2.95 min.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue obtained
  3. custompartitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the product which
  7. customwas purified by preparative TLC (petroleum ether/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b49ed3325e014fe98a2edce52c928c92
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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