Hydrochloric Acid → 1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

HRID 1681869Notes

Reaction equation

HRID 1681869 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[N:3][CH:2]=1.[ClH:10]>O>[ClH:10].[NH:3]1[CH2:4][CH:5]([C:7]([OH:9])=[O:8])[CH2:6][N:1]=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 78346Pyrimidine-5-carboxylic acid

Product 1

HCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochlorideYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyrimidine-5-carboxylic acid (5.0 g, 40 mmol) was suspended in a mixture of 150 ml water and concentrated hydrochloric acid (4.0 g, 40.5 mmol). The mixture was hydrogenated at 26 psig over 1.0 g Pd-on-carbon 10% in a Parr hydrogenator for 3 h. The suspension was filtered and the filter rinsed twice with hot water (20 ml). The filtrate was evaporated in vacuo to give 6.11 g yellow oil (92%). The oil was crystallized from anhydrous methanol/tetrahydrofuran (THF) to give 5.77 g (87%) white crystals in two crops. 300 MHz nmr indicated product.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter rinsed twice with hot water (20 ml)
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-981f88bd9a6c4cc4a6a774037a94f6a5
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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