Hydrochloric Acid → 2-(2,2-Diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride

HRID 1030496Notes

Reaction equation

HRID 1030496 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I.CS[C:19]1[NH:20][CH2:21][CH2:22][CH2:23][N:24]=1.[ClH:25]>CO>[ClH:25].[C:10]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9][C:19]2[NH:24][CH2:23][CH2:22][CH2:21][N:20]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 775752,2-DiphenylethylamineHCID 199998Pyrimidine, 1,4,5,6-tetrahydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 198204702-(2,2-Diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask containing a mixture of 2,2-diphenylethylamine (5.92 g; 3.00×10-2 mole) and 2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (7.74 g, 3.00×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-168° C. for 1.5 hours. The resulting yellow glass was dissolved in methanol. The methanol was evaporated and the resulting yellow oil was dissolved in dichloromethane. This solution was transferred to a separatory funnel where it was washed with 2N aqueous NaOH and saturated aqueous NaCl. After drying over anhydrous Na2SO4, the dichloromethane was evaporated giving a foam which was dissolved in methanol (125 ml). This solution was cooled to 0° C. at which time it was treated with a methanolic solution of HCl. After 10-15 minutes most of the methanol was evaporated and 2-butanone was added. After several days the crystals were collected by filtration. Recrystallization from isopropanol afforded 2-(2,2-diphenylethylamino)-1,4,5,6-tetrahydropyrimidine hydrochloride as off-white crystals: 3.80 g (40%), m.p. 180°-182° C.

Workup

  1. additionA flask containing
  2. customwas immersed in an oil bath
  3. customhad been preheated to ca. 155° C
  4. customThe methanol was evaporated
  5. dissolutionthe resulting yellow oil was dissolved in dichloromethane
  6. customThis solution was transferred to a separatory funnel
  7. washwhere it was washed with 2N aqueous NaOH and saturated aqueous NaCl
  8. dry with materialAfter drying over anhydrous Na2SO4
  9. customthe dichloromethane was evaporated
  10. customgiving a foam which
  11. customAfter 10-15 minutes most of the methanol was evaporated
  12. addition2-butanone was added
  13. filtrationAfter several days the crystals were collected by filtration
  14. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-81b41b2561b0451cb95ab5217392abab
Source dataset
uspto-grants-1992_04
Patent number
US05106845

Reaction notes

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