2-((2-Amino-5-nitropyrimidin-4-yl)amino)ethan-1-ol → 2,5-Diamino-4-(2-hydroxyethylamino)pyrimidine

HRID 273272Notes

Reaction equation

HRID 273272 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1>[Ni].[Fe]>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([NH2:12])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 115139392-((2-Amino-5-nitropyrimidin-4-yl)amino)ethan-1-ol

Product 1

HCID 598384192,5-Diamino-4-(2-hydroxyethylamino)pyrimidine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 23925IronCatalyst

Procedure

As shown in reaction scheme (7) below, 2-amino-4-(2-hydroxyethylamino)-5-nitropyrimidine is reacted with a reducing agent, such as Raney-nickel or iron powder, in a polar organic solvent at a temperature of about 0-100° C., and preferably about 30-50° C., for about 1-10 hours, and preferably about 2-5 hours, to give 2,5-diamino-4-(2-hydroxyethylamino)pyrimidine of formula (XXV). Then, the compound of formula (XXV) is allowed to react immediately without separation, in triethylorthoformate of formula (XVIII) at a temperature of about 50-150° C., and preferably about 70-90° C., for about 5-15 hours, and preferably about 8-10 hours, to give 2-amino-9-(2-hydroxyethyl)purine.

Sources & evidence

ORD record
ord-82f25a0091c74d63a539cb0923efd159
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Reaction notes

Loading…