Dimethylformamide → HCID 49764534, compound

HRID 1022501Notes

Reaction equation

HRID 1022501 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:7](=[O:18])[N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[C:5]2=[O:30].CCOC(C)=O.[CH3:37][N:38](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][N:6]1[C:5](=[O:30])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:37]#[N:38])[CH:3]=2)[N:8]([CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:7]1=[O:18]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 497641526-bromo-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Product 1

HCID 49764534HCID 49764534, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 1.22 g of 6-bromo-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione, 0.3 g of zinc cyanide and 0.089 g of tetrakis(triphenylphosphine)palladium(0) in 10 ml of DMF is irradiated in a microwave field for 3 minutes at 170° C. EtOAc is added and the mixture is washed six times with water. The resulting solution is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (100/0, v/v) to (80/20, v/v) to give 0.804 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 3 minutes at 170° C
  2. washthe mixture is washed six times with water
  3. dry with materialThe resulting solution is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluting with a DCM/EtOAc mixture from (100/0

Sources & evidence

ORD record
ord-0a173ce3b2414b4580b52bd5be71a5b5
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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