Triethylamine → HCID 89494586, compound

HRID 595064Notes

Reaction equation

HRID 595064 reaction equation
Cl[C:2]1[N:3]=[C:4]([Cl:14])[C:5]2[CH:10]([CH3:11])[S:9](=[O:13])(=[O:12])[CH2:8][C:6]=2[N:7]=1.CCN(CC)CC.[CH3:22][C@H:23]1[CH2:28][O:27][CH2:26][CH2:25][NH:24]1>CN(C=O)C>[Cl:14][C:4]1[C:5]2[CH:10]([CH3:11])[S:9](=[O:13])(=[O:12])[CH2:8][C:6]=2[N:7]=[C:2]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][C@@H:23]2[CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 89487102HCID 89487102, compound

Product 1

HCID 89494586HCID 89494586, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (150.0 mg, 0.5926 mmol) and Et3N (119.9 mg, 1.2 mmol) in DMF (2.0 mL) was added (S)-3-methylmorpholine (59.9 mg, 0.6 mmol) dropwise. The reaction mixture stirred overnight, then quenched by addition of H2O and the resulting mixture extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=20:1-2/1) to provide 4-chloro-5-methyl-2-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (B) as a light yellow solid (50 mg, 13.5%). Further elution then provides 2-chloro-5-methyl-4-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (A) as an off-white soild (100 mg, 27%),

Workup

  1. customquenched by addition of H2O
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=20:1-2/1)

Sources & evidence

ORD record
ord-832a062910c54832a54c14e243911ccc
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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