Hydrochloric Acid → HCID 20458252, compound

HRID 544565Notes

Reaction equation

HRID 544565 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]=[C:16]([NH:18][C:19]([NH2:26])=[N:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:15]=[CH:14][N:13]=1)C1C=CC=CC=1.Cl>CCO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]=[C:16]([NH:18][C:19]([NH2:26])=[N:20][CH2:21][C:22]([F:25])([F:23])[F:24])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20458236HCID 20458236, compound

Product 1

HCID 20458252HCID 20458252, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(3-benzyloxypropyl)-4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimidine (3.7 g.) in EtOH (75 ml.) containing concentrated aqueous HCl (1 ml.) was hydrogenated over 5% w/w palladium on carbon (1 g.). The filtrate was evaporated and the residue was partitioned between dilute aqueous NaOH and EtOAc. The EtOAc solution was washed with brine, dried and evaporated and the residue was crystallised from EtOAc to give 2-(3-hydroxypropyl)-4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimidine (0.2 g.), m.p. 136°-138°.

Workup

  1. customThe filtrate was evaporated
  2. customthe residue was partitioned between dilute aqueous NaOH and EtOAc
  3. washThe EtOAc solution was washed with brine
  4. customdried
  5. customevaporated
  6. customthe residue was crystallised from EtOAc

Sources & evidence

ORD record
ord-e4ae57d091cb4ac59c99d4715b740e3b
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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