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

HRID 1626626Notes

Reaction equation

HRID 1626626 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].ClC1N=C(N2CCOC[C@@H]2C)C2CN(C(OCC)=O)CC=2N=1.[F:59]C1C=C(C=CC=1B1OC(C)(C)C(C)(C)O1)N>>[CH2:25]([O:24][C:22]([N:19]1[CH2:21][C:15]2[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])=[N:13][C:12]([C:9]3[CH:8]=[CH:7][C:6]([NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:36])=[CH:11][C:10]=3[F:59])=[N:17][C:16]=2[CH2:18]1)=[O:23])[CH3:28]

Participants

4

Reactant 3

HCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59239149HCID 59239149, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679040(S)-ethyl-2-(4-(3-ethylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 44%

Procedure

Step 1 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 3-fluoro-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 solvent removed in vacuo. The residue was purified by prep HPLC (high pH) yielding the title compound (54.7 mg, 0.13 mmol, 44%).

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 (high pH)

Sources & evidence

ORD record
ord-c7584a3b41d4491e85519836394d602e
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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