1-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → 1-ethyl-3-(3-fluoro-4-(6-methyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626682Notes

Reaction equation

HRID 1626682 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=2[N:7]=1.[CH2:18]([NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[C:26]([F:39])[CH:25]=1)=[O:22])[CH3:19]>>[CH2:18]([NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:3]=[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:5]3[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=3[N:7]=2)=[C:26]([F:39])[CH:25]=1)=[O:22])[CH3:19]

Participants

3

Reactant 2

HCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 866631654-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine2×

Product 1

HCID 666791981-ethyl-3-(3-fluoro-4-(6-methyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 26%

Procedure

Method as example 147 using 4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)morpholine (intermediate 21) and 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 28) as starting materials. The crude reaction mixture was partitioned between EtOAc (25 ml) and water (25 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. Residue was then purified by prep. HPLC at high pH to afford a light yellow solid (61 mg, 0.15 mmol, 26%).

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between EtOAc (25 ml) and water (25 ml)
  3. customThe organic layer was recovered
  4. customthe solvent removed in vacuo
  5. customResidue was then purified by prep

Sources & evidence

ORD record
ord-a8d37baf0e8745089ba1bcd9643cf1ca
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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