Chloride → 9-Ethyl-4-[(2-hydroxyethyl)amino]-7-methylimidazo[5,1-h]-pteridin6(5H)-one

HRID 1460061Notes

Reaction equation

HRID 1460061 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C([O:19][CH2:20][CH2:21][NH:22]CC1C=CC=CC=1)C1C=CC=CC=1.[CH2:30]([C:32]1[NH:33][CH:34]=[C:35]([CH3:37])[N:36]=1)[CH3:31].[Cl-].[C:39](N1C=CN=C1)(N1C=CN=C1)=[O:40].CO.[OH-].[Na+]>[Pd]>[CH2:30]([C:32]1[N:33]2[C:34]([C:39](=[O:40])[NH:8][C:7]3[C:2]([NH:22][CH2:21][CH2:20][OH:19])=[N:3][CH:4]=[N:5][C:6]=32)=[C:35]([CH3:37])[N:36]=1)[CH3:31]

Participants

9

Reactant 7

HCID 312ChlorideHCID 887MethanolHCID 14798Sodium HydroxideHCID 203124,6-Dichloro-5-nitropyrimidineHCID 682631,1'-CarbonyldiimidazoleHCID 5624481-Benzylamino-2-benzyloxyethaneHCID 178437635HCID 178437635, compound

Product 1

HCID 566232119-Ethyl-4-[(2-hydroxyethyl)amino]-7-methylimidazo[5,1-h]-pteridin6(5H)-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared by treatment of 4,6-dichloro-5-nitropyrimidine with N-(2-(benzyloxy)ethyl)benzylamine, followed by reaction with 2ethyl-4-methylimidazole, reduction with fin (II) chloride, cyclization with carbonyldiimidazole, and hydrogenation with palladium on carbon in methanol containing 1.1 eq. NaOH at 50 psi and 50° C. for 24 h.

Workup

  1. customat 50 psi and 50° C.
  2. customfor 24 h.

Sources & evidence

ORD record
ord-8610017ee15a46deae386c6e451c039c
Source dataset
uspto-grants-1998_12
Patent number
US05854419

Reaction notes

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