Methanol → HCID 57591094, compound

HRID 1784089Notes

Reaction equation

HRID 1784089 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:26]=[C:15]3[C:16]4[C:21]([CH2:22][CH2:23][N:14]3[C:13](=[O:27])[N:12]=2)=[CH:20][C:19]([O:24][CH3:25])=[CH:18][CH:17]=4)[CH:7]=[CH:8][CH:9]=1)([O-])=O.CO>CC(O)=O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:26]=[C:15]3[C:16]4[C:21]([CH2:22][CH2:23][N:14]3[C:13](=[O:27])[N:12]=2)=[CH:20][C:19]([O:24][CH3:25])=[CH:18][CH:17]=4)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 57591098HCID 57591098, compound

Product 1

HCID 57591094HCID 57591094, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3-nitro-phenylamino)-9-methoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one (5) (525.4 mg, 1.4 mmol) in AcOH (40 mL), Zn powder (ca. 300 mg) was added and stirred at room temperature for 3 hrs, then at 40° C. overnight. After cooling, MeOH was added to the mixture and insoluble materials were removed by filtration. The MeOH solution was purified on BondElut® SCX (Varian Incorporated) then passed through BondElut® NH2 (Variant Incorporated). Result solid was washed with MeOH to give the title compound (215.1 mg, 46%). MS (ESI) (M+H)+ 335.

Workup

  1. customat 40° C.
  2. customovernight
  3. temperatureAfter cooling
  4. customwere removed by filtration
  5. customThe MeOH solution was purified on BondElut® SCX (Varian Incorporated)
  6. customResult solid
  7. washwas washed with MeOH

Sources & evidence

ORD record
ord-2b11ce1c1196459d9ab1fb7188eaac05
Source dataset
uspto-grants-2009_03
Patent number
US07501512B2

Reaction notes

Loading…