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

HRID 1154387Notes

Reaction equation

HRID 1154387 reaction equation
NC1N(CC2C=CC(Cl)=CC=2)C2N(CC(C)N=2)C(=O)C=1N=O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[NH2:33][C:34]1[N:35]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[C:36]2[N:37]([CH2:44][CH:45]([CH3:47])[N:46]=2)[C:38](=[O:43])[C:39]=1[NH:40][CH:41]=O>C(O)=O>[Cl:55][C:52]1[CH:53]=[CH:54][C:49]([CH2:48][N:35]2[C:34]3[NH:33][CH:41]=[N:40][C:39]=3[C:38](=[O:43])[N:37]3[CH2:44][CH:45]([CH3:47])[N:46]=[C:36]23)=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 146045Sodium dithionateHCID 126838397-amino-8-[(4-chlorophenyl)methyl]-2,3-dihydro-6-formylamino-2-methylimidazo-[1,2-a]pyrimidin-5(8H)-oneHCID 1784298247-amino-8-[(4-chlorophenyl)methyl]-2-methyl-6-nitroso-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 1784298224-[(4-CHLOROPHENYL)METHYL]-6,7-DIHYDRO-6-METHYL-3H-IMIDAZO[1,2-a]PURIN-9(4H)-ONE

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The nitroso compound of Procedure 99 was reduced with sodium dithionate in formic acid according to the method of Procedure 21. The resulting 7-amino-8-[(4-chlorophenyl)methyl]-2,3-dihydro-6-formylamino-2-methylimidazo-[1,2-a]pyrimidin-5(8H)-one, 185 g., (0.54 mole) was then dissolved with heating in 1 l. of 0.6 N NaOH, the solution clarified by filtration, the filtrate acidified with acetic acid, and allowed to cool resulting in precipitation of the desired product, yield 71.7 g., recrystallized from ethylene glycol monomethyl ether/(iPr)2O, m.p. 259°-260.5°.

Workup

  1. dissolution, (0.54 mole) was then dissolved
  2. temperaturewith heating in 1 l
  3. filtrationof 0.6 N NaOH, the solution clarified by filtration
  4. temperatureto cool

Sources & evidence

ORD record
ord-a2923835e8824a50a4434bb6eff8e501
Source dataset
uspto-grants-1984_12
Patent number
US04489078

Reaction notes

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