Sodium Carbonate → HCID 71548327, compound

HRID 595052Notes

Reaction equation

HRID 595052 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[CH2:10][S:9](=[O:12])(=[O:11])[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.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[CH2:10][S:9](=[O:12])(=[O:11])[CH2:8][C:6]=4[N:7]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 894946042-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide

Product 1

HCID 71548327HCID 71548327, compoundYield 11%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide (96 mg, 0.32 mmol) in DME/H2O (4:1, 10 mL) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (106 mg, 0.35 mmol), and Na2CO3 (102 mg, 0.96 mmol) followed by PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was heated to 70° C. and stirred overnight under nitrogen. The solvent was removed under vacuum to give a residue which was partitioned between ethyl acetate and water. The organic layer was separated, dried (Na2SO4) and the solvent removed to give crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (15 mg, 11%).

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed
  7. customto give crude product which
  8. customwas purified by preparative TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-3d2677fad1a34b28ac2d9aa683f2b1ee
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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