Acetic Acid → HCID 20291421, compound

HRID 1863429Notes

Reaction equation

HRID 1863429 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[Br:5][C:6]1[N:7]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18](N)[CH:17]=2)[N:9]2[C:14]=1[CH:13]=[N:12][NH:11][C:10]2=[O:15].C=O.[C:25](O)(=O)C>C(#N)C>[Br:5][C:6]1[N:7]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:2]([CH3:1])[CH3:25])[CH:17]=2)[N:9]2[C:14]=1[CH:13]=[N:12][NH:11][C:10]2=[O:15]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 20291381HCID 20291381, compound

Product 1

HCID 20291421HCID 20291421, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium cyanoborohydride (1.2 gm., 0.019 mole) is added to a stirred solution of 8-bromo-6-(m-aminophenyl)imidazo-[1,5-d]-as-triazine-4(3H)-one, aqueous formaldehyde (5 ml., 37%) in acetonitrile (110 ml.). The reaction mixture is stirred for 15 minutes then acetic acid is added to adjust the pH of the reaction mixture to 7. The reaction mixture is stirred for 45 minutes while the pH of the mixture is maintained at 7 with acetic acid being added as needed. The solvent is then evaporated in vacuo, the residual oil is added to 2 N potassium hydroxide (150 ml.), and crystallizes. The product is washed with water, and recrystallized from acetone-water, m.p. 206° C.(d).

Workup

  1. stirringThe reaction mixture is stirred for 45 minutes while the pH of the mixture
  2. additionadded
  3. customThe solvent is then evaporated in vacuo
  4. additionthe residual oil is added to 2 N potassium hydroxide (150 ml.)
  5. customcrystallizes
  6. washThe product is washed with water
  7. customrecrystallized from acetone-water, m.p. 206° C.(d)

Sources & evidence

ORD record
ord-c9c067e360be4270a19a862ceb40f89c
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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