Ethanol → 9-(1H-imidazol-1-yl)methyl-4-[(2-phenylethyl)amino]imidazo[5,1-h]pteridin-6(5H)-one

HRID 1460066

Reaction equation

HRID 1460066 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C1C=CC=CC=1.N1([C:33]2[NH:34][CH:35]=[C:36]([CH3:38])[N:37]=2)C=CN=C1.[Sn](Cl)Cl.[C:42](N1C=CN=C1)([N:44]1[CH:48]=[CH:47][N:46]=[CH:45]1)=O.C([OH:56])C.[OH-].[Na+]>[Pd]>[N:44]1([CH2:42][C:33]2[N:37]3[C:36]([C:38](=[O:56])[NH:8][C:7]4[C:2]([NH:19][CH2:20][CH2:21][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)=[N:3][CH:4]=[N:5][C:6]=43)=[CH:35][N:34]=2)[CH:48]=[CH:47][N:46]=[CH:45]1

Participants

9

Reactant 7

HCID 702EthanolHCID 14798Sodium HydroxideHCID 203124,6-Dichloro-5-nitropyrimidineHCID 24479Stannous ChlorideHCID 65055N-BenzylphenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178430886HCID 178430886, compound

Product 1

HCID 99081929-(1H-imidazol-1-yl)methyl-4-[(2-phenylethyl)amino]imidazo[5,1-h]pteridin-6(5H)-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared by treatment of 4,6-dichloro-5-nitropyrimidine with N-benzylphenylethylamine, followed by reaction with 2-(1 H-imidazol-1 -yl)-methylimidazole, reduction with tin (II) chloride, cyclization with carbonyidiimidazole, and hydrogenation with palladium on carbon in ethanol containing 1.1 eq. NaOH at 50 psi and 50° C.

Workup

  1. customat 50 psi and 50° C.

Sources & evidence

ORD record
ord-880d68ea11b24ffcba43b4d3163d2f20
Source dataset
uspto-grants-1998_12
Patent number
US05854419

Linked notes

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