Phosgene → HCID 22125161, compound

HRID 1858189Notes

Reaction equation

HRID 1858189 reaction equation
[CH: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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:26](Cl)(Cl)=[O:27].[Cl-].[NH4+]>O1CCCC1>[CH: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:26]2=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 22124968HCID 22124968, compound

Product 1

HCID 22125161HCID 22125161, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 210 mg (0.79 mmol) of 5-cyclohexylaminomethyl-4-methylamino-2-methylthiopyrimidine and 0.2 ml of triethylamine in 10 ml of tetrahydrofuran was added dropwise to an ice-cooled solution of 0.5 ml (0.96 mmol) of phosgene (20% solution in toluene) in 5 ml of tetrahydrofuran. After 1 hour 15 ml of aqueous ammonium chloride solution and 10 ml of tetrahydrofuran were added to the resulting mixture. The phases were separated. The organic phase was dried over magnesium sulfate, filtered and then evaporated. The residue was chromatographed on silica gel using diethyl ether/hexane (3:2) for the elution. Product-containing fractions were combined and evaporated to give 120 mg (52%) of 3-cyclohexyl-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as white solid.

Workup

  1. customThe phases were separated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution
  7. customevaporated

Sources & evidence

ORD record
ord-67432a2ebf554bedbcde68711ca32892
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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