2,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline → (S)-ethyl 2-(4-(3-ethylureido)-2,5-difluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626670Notes

Reaction equation

HRID 1626670 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[C:5]2[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1.[F:23][C:24]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[C:28]([F:40])=[CH:27][C:25]=1[NH2:26]>>[CH2:8]([NH:9][C:11](=[O:12])[NH:26][C:25]1[C:24]([F:23])=[CH:30][C:29]([C:2]2[N:3]=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]3[CH3:22])[C:5]3[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][C:6]=3[N:7]=2)=[C:28]([F:40])[CH:27]=1)[CH3:6]

Participants

3

Reactant 2

HCID 579551442,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)anilineHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679047(S)-ethyl 2-(4-(3-ethylureido)-2,5-difluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 13%

Procedure

Method as described for example 47 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) and 2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. The mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and the solvent removed in vacuo. The residue was purified by prep. HPLC at low pH, yielding the title compound (25 mg, 0.06 mmol, 13%).

Workup

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

Sources & evidence

ORD record
ord-4857dace2a0b4e75a6e82393304dbeaf
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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