Hydrochloric Acid → 2,6-Diamino-7-furan-2-ylmethyl-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one
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[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]#[N:10])[N:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>[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[O:13][CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2-Amino-α-(2-Furanylmethyl)-1,6-dihydro-5-nitro-6-oxo-4-pyrimidineacetonitrile (4.0 g) in 1N NaOH (250 mL) is added sodium dithionite (16 g) and the reaction mixture is heated at 90° C. for 30 min. The reaction mixture is cooled in an ice bath and neutralized with 4N HCl. The resulting precipitate is collected by filtration and purified by a series of acid/base reprecipitations. First the product is reprecipitated from 1N NaOH by acidifying (pH 2) with a saturated solution of oxalic acid. This NaOH/oxalic acid reprecipitation is repeated. Then it is reprecipitated from 1N NaOH by adjusting pH to 11 with 4N HCl. The product 2,6-Diamino-3,5-dihydro-7-(2-furanylmethyl)-4H-pyrrolo [3,2-d]pyrimidin-4-one is dried under vacuum.
Workup
- temperatureThe reaction mixture is cooled in an ice bath
- filtrationThe resulting precipitate is collected by filtration
- custompurified by a series of acid/base reprecipitations
- customFirst the product is reprecipitated from 1N NaOH by acidifying (pH 2) with a saturated solution of oxalic acid
- customThis NaOH/oxalic acid reprecipitation
- customThen it is reprecipitated from 1N NaOH
- dry with materialThe product 2,6-Diamino-3,5-dihydro-7-(2-furanylmethyl)-4H-pyrrolo [3,2-d]pyrimidin-4-one is dried under vacuum
Sources & evidence
- ORD record
- ord-3667218f2cb14037bccf61a3cba8eb72
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05061707
Reaction notes
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