Triethylamine → HCID 22125192, compound

HRID 1858187Notes

Reaction equation

HRID 1858187 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[C:10]([NH:17][CH3:18])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC([O:29][C:30](Cl)(Cl)Cl)=O>O1CCOCC1>[C:1]1([N:7]2[CH2:8][C:9]3[C:10](=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=3)[N:17]([CH3:18])[C:30]2=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 22125083HCID 22125083, compound

Product 1

HCID 22125192HCID 22125192, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 200 mg (0.77 mmol) of 5-phenylaminomethyl-4-methylamino-2-methylthiopyrimidine and 0.2 ml (1.4 mmol) of triethylamine in 15 ml of dioxan was added dropwise to a solution, cooled in ice, of 150 mg (0.79 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. 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate solution were added to the residue. The phases were separated and the dichloromethane phase was dried over magnesium sulfate, filtered and evaporated to give 162 mg (74%) of 3-phenyl-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid.

Workup

  1. additionwas added dropwise to a solution
  2. waitThe mixture was then left
  3. customAfter a further 10 minutes the mixture was evaporated
  4. addition40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate solution were added to the residue
  5. customThe phases were separated
  6. dry with materialthe dichloromethane phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-62e5e2baf2ea4ae684b26795e17535c4
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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