Sodium Carbonate → HCID 71547381, compound

HRID 595055Notes

Reaction equation

HRID 595055 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]2[CH3:20])[C:5]2[CH2:11][S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][C:6]=2[N:7]=1.[CH:21]1([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)=[O:26])[CH2:23][CH2:22]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:21]1([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:2]3[N:3]=[C:4]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]4[CH3:20])[C:5]4[CH2:11][S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][C:6]=4[N:7]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:23][CH2:22]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 62707602HCID 62707602, compound

Product 1

HCID 71547381HCID 71547381, compoundYield 16%

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 (S)-2-chloro-4-(3-methylmorpholino)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6 dioxide (160 mg, 0.5 mmol) in DME/H2O (4:1, 10 mL) were added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (167 mg, 0.55 mmol) and Na2CO3 (159 mg, 1.5 mmol) followed by PdCl2(dppf) (20 mg, 0.025 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 over Na2SO4 filtered and the solvent removed to give a crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (36 mg, 16%).

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 over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customto give a crude product which
  9. customwas purified by preparative TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-e02ee72efd36440eb0427c91fb6285d0
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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