Ethanol → 4-(alpha-Hydroxymethyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

HRID 1003517Notes

Reaction equation

HRID 1003517 reaction equation
C(O)C.[BH4-].[Na+].C([O:8][C:9]([CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)=O)C>O>[OH:8][CH2:9][CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 18796707HCID 18796707, compound

Product 1

HCID 187967884-(alpha-Hydroxymethyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazolineYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of ethanol and 197 mg of sodium borohydride were added to 200 mg of 4-(α-ethoxycarbonyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was refluxed for 30 minutes, followed by the addition of 5 ml of water. The obtained mixture was concentrated under a reduced pressure, followed by the addition of 10 ml of water. The crystal thus precipitated was recovered by filtration. Thus, 30 mg of the title compound was obtained.

Workup

  1. temperatureThe obtained mixture was refluxed for 30 minutes
  2. concentrationThe obtained mixture was concentrated under a reduced pressure
  3. additionfollowed by the addition of 10 ml of water
  4. customThe crystal thus precipitated
  5. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-6b136126f99546cb8340daf65242366d
Source dataset
uspto-grants-2000_04
Patent number
US06046206

Reaction notes

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