Phosgene → 3-(2-methylphenyl)-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858228Notes

Reaction equation

HRID 1858228 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][CH2:13][C:14]1[C:15]([NH:22][CH3:23])=[N:16][C:17]([S:20][CH3:21])=[N:18][CH:19]=1.C(N(CC)CC)C.[Cl-].[NH4+]>O1CCCC1>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:13][C:14]2[C:15](=[N:16][C:17]([S:20][CH3:21])=[N:18][CH:19]=2)[N:22]([CH3:23])[C:1]1=[O:2]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 221251655-(2-Methylphenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine

Product 1

HCID 221251203-(2-methylphenyl)-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-oneYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred solution, cooled in ice, of 0.7 ml (1.3 mmol) of phosgene (20% in toluene) in 5 ml of tetrahydrofuran was treated dropwise with a solution containing 189 mg (0.69 mmol) of 5-(2-methylphenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine and 0.2 ml (1.4 mmol) of triethylamine in 5 ml of tetrahydrofuran. The mixture was stirred for 1 hour. To the mixture were added 20 ml of tetrahydrofuran and 20 ml of saturated aqueous ammonium chloride solution. The phases were separated and the organic phase was dried over magnesium sulfate, filtered and evaporated to give 210 mg (100%) of 3-(2-methylphenyl)-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a cream-colored solid. [Mass spectrum (ESI) MH+ =301].

Workup

  1. additionwas treated dropwise with a solution
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-67753ce1b42742c1b9abf25db4c912e3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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