Triethylamine → HCID 22125067, compound

HRID 1858221Notes

Reaction equation

HRID 1858221 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]1[C:12]([NH:19][CH3:20])=[N:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=1.C(N(CC)CC)C.ClC([O:31][C:32](Cl)(Cl)Cl)=O>O1CCOCC1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N:9]1[CH2:10][C:11]2[C:12](=[N:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=2)[N:19]([CH3:20])[C:32]1=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 22125081HCID 22125081, compound

Product 1

HCID 22125067HCID 22125067, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 195 mg (0.68 mmol) 5-(2,6-dimethylphenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine and 0.19 ml (1.4 mmol) of triethylamine in 10 ml of dioxan was added dropwise to an ice-cooled solution of 0.085 ml (0.7 mmol) of trichloromethyl chloroformate in 10 ml of dioxan. The mixture was then left to warm to room temperature. After a further 10 minutes the mixture was evaporated. To the residue were added 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate. The phases were separated and the dichloromethane phase was dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in 15 ml of pyridine and heated at reflux for 1 hour. The mixture was cooled and evaporated. The residue was partitioned between 20 ml of dichloromethane and 20 ml of 2M hydrochloric acid. The organic phase was washed with 20 ml of water, dried over magnesium sulfate and evaporated to give 100 mg (47%) of 3-(2,6-dimethylphenyl)-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid. [Mass spectrum (ESI) MH+ =315].

Workup

  1. waitThe mixture was then left
  2. customAfter a further 10 minutes the mixture was evaporated
  3. additionTo the residue were added 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate
  4. customThe phases were separated
  5. dry with materialthe dichloromethane phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue was dissolved in 15 ml of pyridine
  9. temperatureheated
  10. temperatureat reflux for 1 hour
  11. temperatureThe mixture was cooled
  12. customevaporated
  13. customThe residue was partitioned between 20 ml of dichloromethane and 20 ml of 2M hydrochloric acid
  14. washThe organic phase was washed with 20 ml of water
  15. dry with materialdried over magnesium sulfate
  16. customevaporated

Sources & evidence

ORD record
ord-1e032eeab2dd4bc7a3471202c8bcbfd1
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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