Ethyl orthoformate → HCID 11777595, compound

HRID 883548Notes

Reaction equation

HRID 883548 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[S:16])[N:6]([CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:7]=1[NH2:8].[CH:18](OCC)(OCC)OCC>CCCCCCC>[CH:10]1([CH2:9][N:6]2[C:7]3[N:8]=[CH:18][NH:1][C:2]=3[C:3](=[O:17])[NH:4][C:5]2=[S:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 86601053HCID 86601053, compound

Product 1

HCID 11777595HCID 11777595, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

5,6-Diamino-1-cyclohexylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, (1.44 g, 5.67 mmol) together with triethyl orthoformate (15 mL) was heated at 146° C. for 2 h and 10 minutes. The mixture was allowed to cool to ambient temperature and then further cooled on an ice-bath, followed by addition of heptane (5 mL). After filtration of the suspension and washing with heptane (20 mL), the obtained solid was dried in vacuo. Suspending the solid (1.2 g) in a hot mixture of 2-propanol (125 mL), water (5 mL) and tert-butyl methyl ether (25 mL) gave, after cooling and filtration, a white precipitate which was washed with further tert-butyl methyl ether (5 mL). The solid was dried in vacuo to give the title compound (0.95 g, 63%).

Workup

  1. temperaturefurther cooled on an ice-bath
  2. filtrationAfter filtration of the suspension
  3. washwashing with heptane (20 mL)
  4. customthe obtained solid was dried in vacuo
  5. additionin a hot mixture of 2-propanol (125 mL), water (5 mL) and tert-butyl methyl ether (25 mL)
  6. customgave
  7. temperatureafter cooling
  8. filtrationfiltration
  9. washa white precipitate which was washed with further tert-butyl methyl ether (5 mL)
  10. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-f480426822fc4452beda613e0abf40ab
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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