Sodium borohydride → 3-(3,4-dimethoxybenzyl)-6-(hydroxymethyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022507Notes

Reaction equation

HRID 1022507 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:18]=[O:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26].[BH4-].[Na+]>CO.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][OH:19])[CH:14]=2)[N:9]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:8]1=[O:26]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866647683-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydro-quinazoline-6-carbaldehyde

Product 1

HCID 667322243-(3,4-dimethoxybenzyl)-6-(hydroxymethyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dioneYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.575 g of the compound obtained in Step 14.2 and 0.077 g of NaBH4 in a mixture of 20 ml of MeOH and 10 ml of THF is stirred for 30 minutes at room temperature. The reaction medium is evaporated under reduced pressure. The residue is taken up in DCM. This solution is washed with saturated NH4Cl solution. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure to give 0.554 g of the expected product.

Workup

  1. customThe reaction medium is evaporated under reduced pressure
  2. washThis solution is washed with saturated NH4Cl solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ab18a858213f4edcb37acf3918ccf432
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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