Hydrochloric Acid → Hydrochloric Acid

HRID 1650163Notes

Reaction equation

HRID 1650163 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]([N+:17]([O-])=O)=[C:6]([CH:8]([CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[C:9]#[N:10])[N:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[ClH:29].[OH-].[NH4+]>[OH-].[Na+]>[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[NH:17][C:9]([NH2:10])=[C:8]([CH2:11][C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)[C:6]=2[N:7]=1.[ClH:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 1359803452-(2-Amino-5-nitro-6-oxo-3,6-dihydropyrimidin-4-yl)-3-(thiophen-3-yl)propanenitrile

Product 2

HCID 313Hydrochloric AcidHCID 1354183612,6-Diamino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo(3,2-d)pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-Amino-1,6-dihydro-5-nitro-6-oxo-α-(3-thienylmethyl)-4-pyrimidineacetonitrile prepared above (5.0 g) in 1N NaOH (300 mL) is added sodium dithionite (20 g). The reaction mixture is heated for 30 min at 90° C. and then is acidified (pH 1) with conc HCl while still hot. The reaction mixture is cooled and neutralized with ammonium hydroxide. The resulting precipitate is collected by filtration, washed with cold water and dried under vacuum. The crude product is added to 100 mL conc HCl in small portions with stirring and the hydrochloride salt is collected by filtration. The product is recrystallized from 1N HCl to give 2,6-Diamino-3,5-dihydro-7-(3-thienylmethyl)-4H-pyrrolo [3,2-d]pyrimidin-4-one as the monohydro-chloride salt (2.35 g), mp>185° C. (dec). ##STR19##

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with cold water
  4. customdried under vacuum
  5. additionThe crude product is added to 100 mL conc HCl in small portions
  6. filtrationthe hydrochloride salt is collected by filtration
  7. customThe product is recrystallized from 1N HCl

Sources & evidence

ORD record
ord-5515ae74c9124206a495711ef061e961
Source dataset
uspto-grants-1990_05
Patent number
US04923872

Reaction notes

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