Hydrochloric Acid → 5-Pyrimidinol, 1,4,5,6-tetrahydro-5-phenyl-, monohydrochloride

HRID 623200Notes

Reaction equation

HRID 623200 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[CH2:6][NH2:7].[CH:15](OCC)=O.O.Cl>C(O)C.CO>[ClH:1].[OH:8][C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][NH:3][CH:15]=[N:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8025Ethyl formateHCID 21290601HCID 21290601, compound

Product 1

HCID 30874735-Pyrimidinol, 1,4,5,6-tetrahydro-5-phenyl-, monohydrochlorideYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture consisting of 5.56 g (0.0335 mol) of 1,3-diamino-2-phenylpropan-2-ol dihydrochloride (m.p. (inst.)=242° C.) and 2.479 g (0.0335 mol; 2.7 ml) of ethyl formate is heated at 100° C. for 3 h. It is then heated at 100° C. under reduced pressure (vacuum obtained by means of a water-jet pump) for 1 h. The reaction medium is cooled, taken up with CH3OH, acidified with ethanol containing HCl and evaporated to dryness, and the evaporation residue is triturated with ether, acetone and chloroform. The precipitate formed is collected by filtration and then recrystallized from an ethanol/diethyl ether mixture (1:1 v/v) to give 6 g (yield: 84%) of CRL 41 382. M.p. (inst.)=206° C.

Workup

  1. temperatureIt is then heated at 100° C. under reduced pressure (vacuum
  2. temperatureThe reaction medium is cooled
  3. customevaporated to dryness
  4. customthe evaporation residue is triturated with ether, acetone and chloroform
  5. customThe precipitate formed
  6. filtrationis collected by filtration
  7. customrecrystallized from an ethanol/diethyl ether mixture (1:1 v/v)
  8. customto give 6 g (yield: 84%) of CRL 41 382
  9. customM.p. (inst.)=206° C.

Sources & evidence

ORD record
ord-f52bc11aee924cf69a8e0c1482ffef4d
Source dataset
uspto-grants-1988_09
Patent number
US04774248

Reaction notes

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