2-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline

HRID 1626578Notes

Reaction equation

HRID 1626578 reaction equation
C(NC(=O)[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][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:16]=3[N:17]=2)=[CH:8][CH:7]=1)C.[F:37]C1C=C(B2OC(C)(C)C(C)(C)O2)C=CC=1N>>[F:37][C:11]1[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][N:19]([CH3:20])[CH2:18][C:16]=3[N:17]=2)[CH:8]=[CH:7][C:6]=1[NH2:5]

Participants

3

Reactant 2

HCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59239149HCID 59239149, compound

Product 1

HCID 66679018(S)-2-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)anilineYield 98%

Procedure

Method as described for intermediate 5 using 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting material. The crude reaction 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 flash SCX2 chromatography affording the title compound (139 mg, 0.40 mmol, 98%).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through a celite 545 pre-packed cartridge (2.5 g)
  3. washwashed with MeOH and solvent
  4. customremoved in vacuo
  5. customThe residue was purified by flash SCX2 chromatography

Sources & evidence

ORD record
ord-29664aee5be1435abfb35c9d200c8fa1
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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