2-(Methylsulfonyl)-4-(tributylstannyl)pyrimidine → 2,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2363980Notes

Reaction equation

HRID 2363980 reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[NH:5][C:4]=2[CH:3]=1.[CH3:14][S:15]([C:18]1[N:23]=[C:22]([Sn](CCCC)(CCCC)CCCC)[CH:21]=[CH:20][N:19]=1)(=[O:17])=[O:16]>O1CCOCC1.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>[CH3:12][C:6]1([CH3:13])[NH:5][C:4]2[CH:3]=[C:2]([C:20]3[CH:21]=[CH:22][N:23]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[N:19]=3)[S:10][C:9]=2[C:8](=[O:11])[NH:7]1

Participants

5

Reactant 2

HCID 142708512-(Methylsulfonyl)-4-(tributylstannyl)pyrimidineHCID 667434256-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 667437202,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.110 g, 0.420 mmol), 2-(methylsulfonyl)-4-(tributylstannyl)pyrimidine (0.225 g, 0.504 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.097 g, 0.084 mmol) in 1,4-dioxane (10 mL) was purged with nitrogen and microwave-irradiated at 150° C. for 1 h. Then, the reaction mixture was cooled, and concentrated with silica gel, and the residue was purified by flash chromatography (Combiflash, silica gel, ethyl acetate) to give the title compound (0.080 g, 56%) as a yellow solid:

Workup

  1. customwas purged with nitrogen
  2. custommicrowave-irradiated at 150° C. for 1 h
  3. temperatureThen, the reaction mixture was cooled
  4. concentrationconcentrated with silica gel
  5. customthe residue was purified by flash chromatography (Combiflash, silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-47beade190d341d780681b46f9bdd65f
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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