Ammonia → 6-(2-aminopyrimidin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2363981Notes

Reaction equation

HRID 2363981 reaction equation
[CH3:1][C:2]1([CH3:22])[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=3)[S:10][C:5]=2[C:4](=[O:21])[NH:3]1.[NH3:23].CO>O1CCOCC1>[NH2:23][C:13]1[N:12]=[C:11]([C:9]2[S:10][C:5]3[C:4](=[O:21])[NH:3][C:2]([CH3:22])([CH3:1])[NH:7][C:6]=3[CH:8]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 667437202,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 667440116-(2-aminopyrimidin-4-yl)-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.044 g, 0.13 mmol) and 7 M ammonia in methanol (2.0 mL, 14 mmol) in 1,4-dioxane (8 mL) was microwave-irradiated at 120° C. for 75 min. Then, the reaction mixture was cooled, and concentrated with silica gel, and the residue was purified twice by flash chromatography (Combiflash, silica gel, ethyl acetate to 90:10 ethyl acetate/methanol) to give the title compound (0.019 g, 53%) as a yellow solid:

Workup

  1. customwas microwave-irradiated at 120° C. for 75 min
  2. temperatureThen, the reaction mixture was cooled
  3. concentrationconcentrated with silica gel
  4. customthe residue was purified twice by flash chromatography (Combiflash, silica gel, ethyl acetate to 90:10 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-ab643242bfa648279a6ed5efacdb7c94
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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