Hydrazine hydrate (1:1) → HCID 136366828, compound

HRID 2076836Notes

Reaction equation

HRID 2076836 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[N:9][CH:10]=2)[N:5]=[C:4]([CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[NH:3]1.O.NN>C(O)C>[NH2:13][CH2:12][C:4]1[NH:3][C:2](=[O:1])[C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[N:9][CH:10]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1363668202-(4-Oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 136366828HCID 136366828, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-(4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione (50 mg, 0.163 mmol) and hydrazine monohydrate (0.25 mL, 5.09 mmol) in ethanol (3 mL) was stirred at ambient temperature for 4 hours. A light yellow solid of 2-amino-isoindole-1.3-dione was filtered off, the filtrate was evaporated and purified by column chromatography (silica gel, EtOAc/MeOH, 1/1) to yield 2-aminomethyl-3H-pyrimido[4,5-d]pyrimidin-4-one (24 mg, 83%) as a off-white solid. MS (m/e): 176.2 [M−H−].

Workup

  1. filtrationA light yellow solid of 2-amino-isoindole-1.3-dione was filtered off
  2. customthe filtrate was evaporated
  3. custompurified by column chromatography (silica gel, EtOAc/MeOH, 1/1)

Sources & evidence

ORD record
ord-9c2c10a7240749f89f9b9c8cd4ef18fa
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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