Potassium Carbonate → Methyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

HRID 532289Notes

Reaction equation

HRID 532289 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([OH:23])[CH:3]=1.Br[CH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:22][O:21][C:19]([C:16]1[S:15][C:11]2[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[O:23][CH2:25][CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:10]=2[C:17]=1[CH3:18])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 58413397Methyl-4-(4-fluoro-2-((tetrahydro-2-H-pyran-4-yl)methoxy)phenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate (100 mg) was dissolved in DMF (2 ml), 4-bromomethyltetrahydropyran (107 mg) and potassium carbonate (83 mg) were added. The reaction was stirred at 60° C. overnight. Then the reaction mixture was diluted with EtOAc and washed with water and brine. The solvent was removed in vacuo and the residue triturated with Et2O.

Workup

  1. washwashed with water and brine
  2. customThe solvent was removed in vacuo
  3. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-22c55cc77b7345d5b40f514fd32d9780
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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