Dimethylformamide → HCID 136101835, compound

HRID 249980Notes

Reaction equation

HRID 249980 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][N:7]=[C:6]2[NH:14][CH:15]([CH3:17])[CH3:16].CN(C)C=O>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[OH:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][CH:15]([CH3:17])[CH3:16])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:2]=[O:1]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 136101839HCID 136101839, compound

Product 1

HCID 136101835HCID 136101835, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

6-(Hydroxymethyl)-4-(isopropylamino)quinazoline-7-ol (510 mg, 2.19 mmol) is dissolved in 50 mL of toluene and 5 mL of dimethylformamide and at room temperature admixed portionwise with manganese(IV) oxide (1.9 g, 21.9 mmol). After 24 hours the batch is filtered through Celite and washed with dichloro-methane/methanol 9/1. Removal of the solvent and also chromatographic purification (silica gel, dichloromethane/methanol: 0→50% methanol) gives the desired product in 56% yield (280 mg).

Workup

  1. customat room temperature
  2. filtrationAfter 24 hours the batch is filtered through Celite
  3. washwashed with dichloro-methane/methanol 9/1
  4. customRemoval of the solvent and also chromatographic purification (silica gel, dichloromethane/methanol: 0→50% methanol)

Sources & evidence

ORD record
ord-593d08c528a445219bfef345e06e79d0
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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