Triethylamine → HCID 68526018, compound

HRID 1988585Notes

Reaction equation

HRID 1988585 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH2:12][C:13]1[C:14]([NH2:21])=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=1.C(N(CC)CC)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:12][C:13]2[C:14](=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=2)[NH:21][C:30]1=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 24747271HCID 24747271, compound

Product 1

HCID 68526018HCID 68526018, compoundYield 218.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-[(2-methyl-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine (112 mg, 0.37 mmol) and triethylamine (112 μL, 0.80 mmol) in THF (5 mL) is added a solution of triphosgene (38 mg, 0.13 mmol) in THF (1 mL) at 0° C., and the mixture is stirred for 3 hours at room temperature. The reaction mixture is diluted with EtOAc (10 mL), and washed with saturated aqueous sodium bicarbonate solution. The organic layer is dried over MgSO4, concentrated under reduced pressure and recrystallized from dichloromethane to give 3-(2-methyl-5-nitro-phenyl)-7-methylsulfanyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (94 mg, 76%) as a white crystalline solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customrecrystallized from dichloromethane

Sources & evidence

ORD record
ord-102766ae78df4134adf235a63354c392
Source dataset
uspto-grants-2010_01
Patent number
US07642255B2

Reaction notes

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