Sodium Carbonate → HCID 71547537, compound

HRID 595060Notes

Reaction equation

HRID 595060 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[C:5]2[S:10](=[O:12])(=[O:11])[CH2:9][CH2:8][C:6]=2[N:7]=1.[CH:20]1([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)=[O:25])[CH2:22][CH2:21]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:20]1([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]4[CH3:19])[C:5]4[S:10](=[O:12])(=[O:11])[CH2:9][CH2:8][C:6]=4[N:7]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:22][CH2:21]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 89494575HCID 89494575, compound

Product 1

HCID 71547537HCID 71547537, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To solution of 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6,7-dihydrothieno[3,2-d]pyrimidine 5,5-dioxide (50 mg, 0.16 mmol), in 2.0 mL of DME/H2O (4/1, v/v) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (59.7 mg, 0.20 mmol) and Na2CO3 (52.3 mg, 0.49 mmol). The mixture was degassed twice, and then catalytic amount of Pd(dppf)Cl2 (10 mg, 0.013 mmol) was added. The mixture was heated to 80° C. and stirred for 3 h under nitrogen. The resulting mixture was then cooled and diluted with EtOAc and H2O the aqueous layer was extracted with ethyl acetate and the combined organic layers were combined, washed by brine, dried over anhydrous Na2SO4, filtered, and then evaporated to give the crude which was purified by column chromatography on silica gel (eluent: CH2Cl2/ethyl acetate=30/1˜1/1) to provide 1-cyclopropyl-3-[4-[4-[(3S)-3-methylmorpholin-4-yl]-5,5-dioxo-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl]phenyl]urea as a white solid, (30.0 mg, 41%).

Workup

  1. customThe mixture was degassed twice
  2. temperatureThe resulting mixture was then cooled
  3. extractionwas extracted with ethyl acetate
  4. washwashed by brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude which
  9. customwas purified by column chromatography on silica gel (eluent: CH2Cl2/ethyl acetate=30/1˜1/1)

Sources & evidence

ORD record
ord-1e5494d15143476a8642fd90218c375a
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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