Sodium Carbonate → Tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-yloxy)piperidin-1-carboxylate

HRID 532487Notes

Reaction equation

HRID 532487 reaction equation
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([O:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:5]=2[S:4][CH:3]=1.[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)(=[O:28])=[O:27].C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([C:2]2[C:6]3[N:7]=[CH:8][N:9]=[C:10]([O:11][CH:12]4[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]4)[C:5]=3[S:4][CH:3]=2)=[CH:31][CH:30]=1)(=[O:28])=[O:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 68299345Tert-butyl 4-(7-bromothieno[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 57415237Tert-butyl 4-(7-(4-methanesulfonylphenyl)thieno[3,2-d]pyrimidin-4-yloxy)piperidin-1-carboxylateYield 21.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl 4-(7-bromothieno[3,2-d]pyrimidin-4-yloxy)piperidine-1-carboxylate (100 mg), 4-methanesulfonyl-phenylboronic acid (72 mg), Pd(PPh3)4 (17 mg) and 2N Na2CO3 (0.72 mL) were added to 1,4-dioxane (2 mL), and stirred at 100° C. for 12 hours in a hermetically sealed reactor. The reaction mixture was cooled to room temperature, extracted with ethyl acetate and distilled water, and the organic layer thus obtained was washed with water and a saline solution. Subsequently, the washed organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (25 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. distillationdistilled water
  4. customthe organic layer thus obtained
  5. washwas washed with water
  6. dry with materialSubsequently, the washed organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-010bdb0c15e44f37a97dd9365cea8618
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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