Dimethyl Sulfoxide → HCID 44602516, compound

HRID 448540Notes

Reaction equation

HRID 448540 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][CH2:12][CH2:13][C:14]1[C:19](=[O:20])[N:18]2[CH2:21][CH2:22][CH2:23][CH:24]([OH:25])[C:17]2=[N:16][C:15]=1[CH3:26].C(N(CC)CC)C>ClCCl>[Cl:11][CH2:12][CH2:13][C:14]1[C:19](=[O:20])[N:18]2[CH2:21][CH2:22][CH2:23][C:24](=[O:25])[C:17]2=[N:16][C:15]=1[CH3:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 155471943-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 44602516HCID 44602516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalylchloride (8.8 ml) in dichloromethane (20 ml) was cooled to −65° C. and a solution of dimethyl sulfoxide (6.5 ml) dissolved in dichloromethane (20 ml) was added to it slowly and stirred for 30 min. keeping the temperature at −65° C. a solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (5 grams) (formula-7) dissolved in dichloromethane (30 ml) was added to it very slowly and stirred for 40 min. Triethyl amine was added to the reaction mixture and then quenched with water. The organic layer was separated, washed with aqueous sodium carbonate and water. The solvent from the organic layer was distilled off under reduced pressure to provide the title compound.

Workup

  1. additionwas added to it slowly
  2. customat −65° C.
  3. additionwas added to it very slowly
  4. stirringstirred for 40 min
  5. customquenched with water
  6. customThe organic layer was separated
  7. washwashed with aqueous sodium carbonate and water
  8. distillationThe solvent from the organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0768b6b37ae74e278e21280929a41dd7
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

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