1-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (R)-tert-butyl 2-(4-(3-cyclopropylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

HRID 1626706Notes

Reaction equation

HRID 1626706 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.[CH:25]1([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[C:34]([F:47])[CH:33]=2)=[O:30])[CH2:27][CH2:26]1>>[CH:25]1([NH:28][C:29](=[O:30])[NH:31][C:32]2[CH:37]=[CH:36][C:35]([C:2]3[N:3]=[C:4]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][C@H:19]4[CH3:24])[C:5]4[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=4[N:7]=3)=[C:34]([F:47])[CH:33]=2)[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 666792291-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 86663173(R)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Product 1

HCID 66679060(R)-tert-butyl 2-(4-(3-cyclopropylureido)-2-fluorophenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylateYield 78%

Procedure

Method as described for example 147 using (R)-tert-butyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (from step 1) and 1-cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 29) as starting materials. Reaction solvent was removed in vacuo. The residue was then partitioned between DCM (100 ml) and water (80 ml). The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by flash chromatography using 20-100% ethyl acetate/petroleum ether 40-60 to yield an off white solid (1.107 g, 2.16 mmol, 78%).

Workup

  1. customReaction solvent
  2. customwas removed in vacuo
  3. customThe residue was then partitioned between DCM (100 ml) and water (80 ml)
  4. customThe organic layer was recovered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4d496f85a8e24e59b99deadcd1a073c0
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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