Hydrochloric Acid → HCID 135400900, compound

HRID 1029383Notes

Reaction equation

HRID 1029383 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:21])[C:5]([N+:18]([O-])=O)=[C:6]([CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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:21])[C:5]2[NH:18][C:9]([NH2:10])=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 135544558HCID 135544558, compound

Product 1

HCID 135400900HCID 135400900, compound

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-(phenylmethyl)-4-pyrimidine acetonitrile as prepared above (10.0 g) in 1N NaOH (600 mL) is added sodium dithionite (35 g). The reaction mixture is heated at 90° C. for 35 min and is acidified to pH 4 with 4N HCl while still hot. The reaction mixture is cooled in an ice bath and the precipitate is collected by filtration. It is dried over P2O5 under vacuum (4.0 g). The crude (undecarboxy-ated) product is dissolved in 300 mL conc HCl and quickly filtered through a glass frit before it crystallized out. The resulting suspension is boiled for five minutes and cooled. The product 2,6-Diamino-3, 5-dihydro-7-(phenylmethyl)-4H-pyrrolo[3,2-d]is collected by filtration (1.98 g, 23%) mp>250° C. (dec). ##STR13##

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. filtrationthe precipitate is collected by filtration
  3. dry with materialIt is dried over P2O5 under vacuum (4.0 g)
  4. dissolutionThe crude (undecarboxy-ated) product is dissolved in 300 mL conc HCl
  5. filtrationquickly filtered through a glass frit before it
  6. customcrystallized out
  7. temperaturecooled
  8. filtrationThe product 2,6-Diamino-3, 5-dihydro-7-(phenylmethyl)-4H-pyrrolo[3,2-d]is collected by filtration (1.98 g, 23%) mp>250° C. (dec)

Sources & evidence

ORD record
ord-5f8f5e5b972a4dd3bbd28b4839712985
Source dataset
uspto-grants-1992_04
Patent number
US05102879

Reaction notes

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