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

HRID 1626689Notes

Reaction equation

HRID 1626689 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[CH2:10][N:9]([C:11](=[O:13])[CH3:12])[CH2:8][C:6]=2[N:7]=1.[CH2:20]([NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[C:28]([F:41])[CH:27]=1)=[O:24])[CH3:21]>>[C:11]([N:9]1[CH2:10][C:5]2[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:3][C:2]([C:29]3[CH:30]=[CH:31][C:26]([NH:25][C:23]([NH:22][CH2:20][CH3:21])=[O:24])=[CH:27][C:28]=3[F:41])=[N:7][C:6]=2[CH2:8]1)(=[O:13])[CH3:12]

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 866631671-(2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethanone2×

Product 1

HCID 666789801-(4-(6-acetyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)-3-fluorophenyl)-3-ethylureaYield 8%

Procedure

Method as described for example 147 using 1-(2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethanone (intermediate 23) and 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) (intermediate 28) as starting materials. The crude reaction mixture was purified by SCX-2 cartridge (loaded in MeOH eluted with 2M methanolic ammonia). Ammonia eluent was concentrated in vacuo. Residue was then purified by prep. HPLC at high pH to afford an off white solid (17.4 mg, 0.04 mmol, 8%).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by SCX-2 cartridge (loaded in MeOH eluted with 2M methanolic ammonia)
  3. concentrationAmmonia eluent was concentrated in vacuo
  4. customResidue was then purified by prep

Sources & evidence

ORD record
ord-de5bb6cf8c16467e855d9d2b8bbae04b
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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