Sodium Carbonate → HCID 71547383, compound

HRID 595054Notes

Reaction equation

HRID 595054 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:5]2[CH2:11][S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[CH:19]1([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)=[O:24])[CH2:21][CH2:20]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:19]1([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:2]3[N:3]=[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]4[CH3:18])[C:5]4[CH2:11][S:10][CH2:9][CH2:8][C:6]=4[N:7]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:21][CH2:20]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 62707601HCID 62707601, compound

Product 1

HCID 71547383HCID 71547383, compoundYield 27%

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 (100 mg, 0.35 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 (116 mg, 0.38 mmol) and Na2CO3 (111 mg, 1.05 mmol) followed by PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was stirred overnight at 70° C. 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 evaporated to give the crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (40 mg, 27%).

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. customevaporated
  8. customto give the crude product which
  9. customwas purified by preparative TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-00c8fc515dc6405f8781ff8002b8027f
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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