Triethylamine → HCID 89494611, compound

HRID 595072Notes

Reaction equation

HRID 595072 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:11][CH2:10][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[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12012220(3S)-3-methylmorpholineHCID 133072142,4-Dichloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine

Product 1

HCID 89494611HCID 89494611, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine (500 mg, 2.26 mmol) and Et3N (457 mg, 4.52 mmol) in DMF (5.0 mL) at 0° C. was added 3-(S)-methylmorpholine (252 mg, 2.49 mmol) dropwise. The reaction was stirred overnight at rt, then the solvent removed under vacuum to give a residue which was partitioned between water and ethyl acetate. The organic layer was separated, dried and concentrated to give the crude product which was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=10/1) to give 2-chloro-7,8-dihydro-4-((S)-3-methylmorpholino)-6H-thiopyrano[3,2-d]pyrimidine (380 mg, 87%) as a light yellow solid.

Workup

  1. customthe solvent removed under vacuum
  2. customto give a residue which
  3. customwas partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customwas purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-e56ee38a5fd648808cb490dcf1a650d2
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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