1-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → HCID 66679190, compound

HRID 1626632Notes

Reaction equation

HRID 1626632 reaction equation
[CH2:1]([NH:3][C:4](=[O:36])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[C:15]3C[CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])(C)C)=[O:23])[CH2:18][C:16]=3[N:17]=2)=[CH:8][CH:7]=1)[CH3:2].Cl[C:38]1[N:39]=[C:40](N2CCOC[C@@H]2C)[C:41]2CN(C(OCC)=O)CC=2N=1.N1C=CC=C(NC(NC2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=O)C=1>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]>[CH3:35][C@@H:30]1[N:29]([C:14]2[C:15]3[CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:28])=[O:23])[CH2:18][C:16]=3[N:17]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:4]([NH:3][C:1]4[CH:38]=[N:39][CH:40]=[CH:41][CH:2]=4)=[O:36])=[CH:7][CH:8]=3)[N:13]=2)[CH2:34][CH2:33][O:32][CH2:31]1

Participants

5

Reactant 3

HCID 446075271-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 59239149HCID 59239149, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679190HCID 66679190, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Method as described for intermediate 5 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) and 1-(pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea as starting materials, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and reduced in vacuo. The residue was purified first by flash chromatography using a gradient of 0-40% DCM/MeOH, then triturating with a mixture of petrol ether/ethyl acetate (9:1) affording the title compound after filtration and drying of the solid obtained (23 mg, 0.05 mmol, 30%).

Workup

  1. filtrationThe reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  2. washwashed with MeOH
  3. customThe residue was purified first by flash chromatography
  4. customtriturating with a mixture of petrol ether/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-a3f1529ccf8748b5a1306e3c710d66ed
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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