Hydrazine hydrate (1:1) → HCID 135433598, compound

HRID 864986Notes

Reaction equation

HRID 864986 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[NH:10][CH:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3Cl)[C:6]=2[N:7]=1.O.NN>C(O)C.[Pd]>[NH2:1][C:2]1[NH:3][C:4](=[O:19])[C:5]2[NH:10][CH:9]=[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 2

HCID 24654Hydrazine hydrate (1:1)HCID 135474256HCID 135474256, compound

Product 1

HCID 135433598HCID 135433598, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-amino-3,5-dihydro-7-(2-chlorophenylmethyl)-4H-pyrrolo[3,2-d]pyrimidin-4-one (0.5 g, 1.8 mmol) in hot ethanol (80 mL) is treated with 30% Pd-C (1.0 g) under N2 and then hydrazine monohydrate (1.5 mL) is added dropwise during a period of 10 minutes. The reaction mixture is held at reflux for 16 hours and then filtered hot through Celite. The filtrate is evaporated to dryness, and the residue triturated and sonicated with H2O (3 mL). The product is collected, washed with H2O and dried to yield 2-amino-3,5-dihydro-7-(phenylmethyl)-4H-pyrrolo[3,2-d]-pyrimidin-4-one melting at 269°-270° C. dec.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationfiltered hot through Celite
  3. customThe filtrate is evaporated to dryness
  4. customthe residue triturated
  5. customsonicated with H2O (3 mL)
  6. customThe product is collected
  7. washwashed with H2O
  8. customdried

Sources & evidence

ORD record
ord-f3ef253a834744bca97a1b7234a8c02a
Source dataset
uspto-grants-1996_10
Patent number
US05565463

Reaction notes

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