Methane → 5-[(4-CHLOROPHENYL)METHYL]-6,7-DIHYDRO-3H-IMIDAZO[1,2-a]PURIN-9(5H)-ONE

HRID 236013

Reaction equation

HRID 236013 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:12][CH2:11][N:5]2[C:6](=[O:10])[C:7]=1[N:8]=O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O.[OH-].[Na+].[CH4:35]>C(O)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:13]2[C:4]3=[N:3][C:2]4[NH:1][CH:35]=[N:8][C:7]=4[C:6](=[O:10])[N:5]3[CH2:11][CH2:12]2)=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 297MethaneHCID 962WaterHCID 14798Sodium HydroxideHCID 146045Sodium dithionateHCID 133914207-AMINO-1-[(4-CHLOROPHENYL)METHYL]-2,3-DIHYDRO-6-NITROSOIMIDAZO-[1,2-a]PYRIMIDIN-5-(1H)-ONE

Product 1

HCID 1785152595-[(4-CHLOROPHENYL)METHYL]-6,7-DIHYDRO-3H-IMIDAZO[1,2-a]PURIN-9(5H)-ONE

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The nitroso compound of Procedure 92 was reduced with sodium dithionate in formic acid according to the method of Procedure 21. The resulting 6-formylamino compound, 1.3 g. (0.0041 mole), was suspended in 40 ml. of water containing 0.0043 mole of NaOH and the mixture was heated on the steam bath until dissolution occurred. The solution was treated with charcoal, filtered, cooled and acidified with HOAc to yield the desired product, 0.85 g., recrystallized from MeOH, yield 0.60 g., hemihydrate m.p. 314°-316° d.

Workup

  1. filtrationfiltered
  2. temperaturecooled

Sources & evidence

ORD record
ord-77a9c18da01248bb9fb938dc6cfcda5a
Source dataset
uspto-grants-1987_02
Patent number
US04642345

Linked notes

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