Tributylphosphine → HCID 66732267, compound

HRID 1022499Notes

Reaction equation

HRID 1022499 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].[CH2:31]([O:38][CH:39]1[CH2:42][NH:41][CH2:40]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(C)([O-])C.[Na+].C(P(CCCC)CCCC)CCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:31]([O:38][CH:39]1[CH2:40][N:41]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:7](=[O:18])[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:5]3=[O:30])[CH2:42]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 23676156Sodium t-butoxideHCID 252206903-(Phenylmethoxy)azetidineHCID 497641526-bromo-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Product 1

HCID 66732267HCID 66732267, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.2 g of 6-bromo-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione, 0.096 g of 3-benzyloxyazetidine, 0.006 g of palladium acetate, 0.055 g of sodium tert-butoxide and 0.01 ml of tributylphosphine in 4 ml of DMF is stirred for 4 days at room temperature. The reaction mixture is 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 (20/80, v/v) to give 0.041 g of the expected product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated under reduced pressure
  3. customThe residue is chromatographed on silica gel
  4. washeluting with a DCM/EtOAc mixture from (100/0

Sources & evidence

ORD record
ord-21a0b1231cd6425c884f395b1cc85b47
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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