HCID 59239149, compound → (S)-ethyl 4-(3-methylmorpholino)-2-(4-(3-(pyridin-4-yl)ureido)phenyl)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626635Notes

Reaction equation

HRID 1626635 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]3[CH2:21]C[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(NC(NC2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=O)=CC=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[CH2:21][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:41]=[CH:40][N:39]=[CH:38][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 59239149HCID 59239149, compoundHCID 666878001-(Pyridin-4-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66678952(S)-ethyl 4-(3-methylmorpholino)-2-(4-(3-(pyridin-4-yl)ureido)phenyl)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 49%

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-4-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 mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and solvent removed in vacuo. The residue was purified by prep HPLC (low pH) yielding the title compound (38.2 mg, 0.08 mmol, 49%).

Workup

  1. filtrationThe mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  2. washwashed with MeOH and solvent
  3. customremoved in vacuo
  4. customThe residue was purified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-1a02fa93649044f0946c4d055b5e6e32
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…