5-Aminopentan-1-ol → HCID 12783829, compound

HRID 980898Notes

Reaction equation

HRID 980898 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.N[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>N1C=CC=CC=1>[OH:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 756345-Aminopentan-1-olHCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one

Product 1

HCID 12783829HCID 12783829, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 3-(6-methyl-3-pyridyl)propionate was reacted at 0° with ethyl formate and sodium hydride in 1,2-dimethoxyethane to give ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate, m.p. 142°-144°, which was heated under reflux with dried nitroguanidine and sodium methoxide in methanol to give 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone, m.p. 215°-6° (decomp). p (ii) Reaction of 2-nitroamino-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone with 5-aminopentanol in refluxing pyridine gives 2-(5-hydroxypentylamino)-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone which can be converted into 2-[5-(O-isoureido)pentylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone by the procedure of Example 5(iii).

Sources & evidence

ORD record
ord-a7f5cf23ad2d41fd9e6774ea7cfd0199
Source dataset
uspto-grants-1987_01
Patent number
US04639519

Reaction notes

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