Triethylamine → HCID 62707601, compound

HRID 595053Notes

Reaction equation

HRID 595053 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.CCN(CC)CC.[CH3:20][C@H:21]1[CH2:26][O:25][CH2:24][CH2:23][NH:22]1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][C@@H:21]2[CH3:20])[C:5]2[CH2:11][S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 158951192,4-Dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine

Product 1

HCID 62707601HCID 62707601, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine (200 mg, 0.9 mmol), and Et3N (182 mg, 1.8 mmol) in DMF (3 mL) at 0° C. was added 3-(S)-methylmorpholine (100 mg, 0.99 mmol). The resultant mixture was stirred at rt overnight. 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 and concentrated to give the product which was purified by preparative TLC (petroleum ether/ethyl acetate=2/1) to produce (S)-2-chloro-4-(3-methylmorpholino)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine (150 mg, 58%).

Workup

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

Sources & evidence

ORD record
ord-a26cc07318e3491caaa8d4347ee57628
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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