1-Cyclopropyl-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-cyclopropylurea

HRID 1626692Notes

Reaction equation

HRID 1626692 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.[CH:20]1([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[C:29]([F:42])[CH:28]=2)=[O:25])[CH2:22][CH2:21]1>>[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:30]3[CH:31]=[CH:32][C:27]([NH:26][C:24]([NH:23][CH:20]4[CH2:22][CH2:21]4)=[O:25])=[CH:28][C:29]=3[F:42])=[N:7][C:6]=2[CH2:8]1)(=[O:13])[CH3:12]

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

Product 1

HCID 666792401-(4-(6-Acetyl-4-morpholino-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)-3-fluorophenyl)-3-cyclopropylureaYield 15%

Procedure

Method as described for (S)-1-cyclopropyl-3-(3-fluoro-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea(example 147) using 1-(2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)ethanone (intermediate 23) and 1-cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 29). Residue was then purified by prep. HPLC at high pH to afford a cream solid (15% yield).

Workup

  1. customResidue was then purified by prep

Sources & evidence

ORD record
ord-24600443c2d14d2b8b2170bcd6b10bcb
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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