HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → 7-(4-Methanesulfonyl-phenyl)-4-methylsulfanylthieno[3,2-d]pyrimidine

HRID 532465
Notes
Print preview

Reaction equation

HRID 532465 reaction equation
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=2[S:4][CH:3]=1.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])=[O:15].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>[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:6]3[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=3[S:4][CH:3]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 469284277-Bromo-4-methylsulfanylthieno[3,2-d]pyrimidine

Product 1

HCID 682993217-(4-Methanesulfonyl-phenyl)-4-methylsulfanylthieno[3,2-d]pyrimidineYield 77.3%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

7-bromo-4-methylsulfanylthieno[3,2-d]pyrimidine (270 mg, 1.0 mmol) was added to 1,4-dioxane (10 mL), and 4-methanesulfonyl-phenylboronic acid (310 mg, 1.6 mmol), tetrakis(triphenylphosphine)palladium(0) (71 mg, 0.062 mmol), and 2N aqueous sodium carbonate (3.1 mL, 3.1 mmol) were sequentially added thereto. The air present in the reaction mixture was removed using a nitrogen balloon, and the reaction mixture was heated to 100° C. and stirred for 4 hours. The reaction was terminated by addition of sodium bicarbonate, and the reaction mixture was extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a foamy residue. The residue was crystallized in the presence of diethyl ether to obtain the title compound (260 mg) as a yellowish solid.

Workup

  1. additionwere sequentially added
  2. customThe air present in the reaction mixture was removed
  3. customThe reaction was terminated by addition of sodium bicarbonate
  4. extractionthe reaction mixture was extracted twice with ethyl acetate
  5. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a foamy residue
  8. customThe residue was crystallized in the presence of diethyl ether

Sources & evidence

ORD record
ord-966ee56e458447039612c1857962c001
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853213B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes