2-Nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate → 2-Amino-1,4,5,6-tetrahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate formate

HRID 1074155Notes

Reaction equation

HRID 1074155 reaction equation
[CH:1]1([C:7]2([C:13]([O:15][CH:16]3[CH2:21][NH:20][C:19](=[N:22][N+]([O-])=O)[NH:18][CH2:17]3)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)=O.[Pd]>[CH:13]([OH:15])=[O:14].[CH:1]1([C:7]2([C:13]([O:15][CH:16]3[CH2:21][NH:20][C:19]([NH2:22])=[N:18][CH2:17]3)=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 1356181062-Nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate

Product 1

HCID 221559172-Amino-1,4,5,6-tetrahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate formateYield 155.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

A solution of 2-nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate (0.45 g) in formic acid (20 ml) was quickly dropped into a flask containing 10% palladium on carbon (0.4 g). The reaction mixture was stirred at room temperature overnight. The catalyst was filtered off, the solvent was removed and the residue was triturated with diethyl ether, affording 0.35 g of 2-amino-1,4,5,6-tetrahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate formate. M.p. 160°-165° C. (dec.).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed
  3. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5820b96a8cd8435097b2d9ed25cf1786
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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