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

HRID 1626581Notes

Reaction equation

HRID 1626581 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]3C[CH2:20][N:19]([C:22]([O:24][C:25](C)([CH3:27])C)=[O:23])[CH2:18][C:16]=3[N:17]=2)=[CH:8][CH:7]=1)C.ClC1N=C(N2CCOC[C@@H]2C)C2CN(C(OCC)=O)CC=2N=1.[F:59]C1C=C(B2OC(C)(C)C(C)(C)O2)C=CC=1N>>[NH2:5][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[CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:27])=[O:23])[CH2:18][C:16]=3[N:17]=2)=[CH:8][C:7]=1[F:59]

Participants

4

Reactant 3

HCID 179061722-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59239149HCID 59239149, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679065(S)-ethyl 2-(4-amino-3-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 88%

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 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. 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 by flash SCX2 chromatography affording the title compound (130 mg, 0.32 mmol, 88%).

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 by flash SCX2 chromatography

Sources & evidence

ORD record
ord-3b2b4e2f5d8e40a9a54a38c3d05e57f6
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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