Cesium carbonate → {[3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrile

HRID 1022480Notes

Reaction equation

HRID 1022480 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)[C:8]1=[O:25].Br[CH2:32][C:33]#[N:34].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:32][C:33]#[N:34])[CH:14]=2)[N:9]([CH:19]2[CH2:20][CH2:21][S:22][CH2:23][CH2:24]2)[C:8]1=[O:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 497642813-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 46937246{[3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]oxy}acetonitrileYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.16 g of the compound obtained in Step 3.3, 0.054 g of bromoacetonitrile and 0.243 g of Cs2CO3 in 1 ml of DMF is irradiated in a microwave field for 15 minutes at 100° C. The reaction mixture is evaporated under reduced pressure. The residue is taken up in DCM, washed with water, dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an EtOAc/DCM mixture from (10/90, v/v) to (20/80, v/v) to give 0.138 mg of the expected product.

Workup

  1. customis irradiated in a microwave field for 15 minutes at 100° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is chromatographed on silica gel
  8. washeluting with an EtOAc/DCM mixture from (10/90

Sources & evidence

ORD record
ord-c14433fcdb1f47c98d99788780a1f2b7
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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