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

HRID 1154381Notes

Reaction equation

HRID 1154381 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-92b9b82a592d49caa3b0b1fa5f24f8ab
Source dataset
uspto-grants-1984_12
Patent number
US04489078

Reaction notes

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