2-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-tert-butyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626579Notes

Reaction equation

HRID 1626579 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]2[CH3:24])[C:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1.[F:25][C:26]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:29][C:27]=1[NH2:28]>>[NH2:28][C:27]1[CH:29]=[CH:30][C:31]([C:2]2[N:3]=[C:4]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]3[CH3:24])[C:5]3[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=3[N:7]=2)=[CH:32][C:26]=1[F:25]

Participants

3

Reactant 2

HCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86663148(S)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate2×

Product 1

HCID 66679191(S)-tert-butyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 22%

Procedure

Method as intermediate 5 using (S)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 1) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (0-80% EtOAc/Petroleum Ether 40-60) to yield a white solid (660 mg, 1.54 mmol, 22%).

Workup

  1. customThe crude reaction mixture
  2. customwas then partitioned between water and EtOAc
  3. customthe phases separated
  4. washthe organic layer washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by flash chromatography (0-80% EtOAc/Petroleum Ether 40-60)

Sources & evidence

ORD record
ord-05d0f5af727d4465a7433232a597fc1b
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…