(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 86703232, compound

HRID 2204413Notes

Reaction equation

HRID 2204413 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)[N:11]([C:14]3[N:15]([CH3:21])[N:16]=[C:17]([CH3:20])[C:18]=3[F:19])[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1[N:37]=[C:36]([O:38][CH3:39])[C:35](B(O)O)=[CH:34][N:33]=1.BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.COC1C(B2OC(C)(C)C(C)(C)O2)=CN=C(N)N=1>>[CH3:30][O:31][C:32]1[N:37]=[C:36]([O:38][CH3:39])[C:35]([C:2]2[N:6]([CH:7]([CH3:8])[CH3:9])[C:5]3[CH:10]([C:22]4[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=4)[N:11]([C:14]4[N:15]([CH3:21])[N:16]=[C:17]([CH3:20])[C:18]=4[F:19])[C:12](=[O:13])[C:4]=3[CH:3]=2)=[CH:34][N:33]=1

Participants

5

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 591984044-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amineHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703233HCID 86703233, compound

Product 1

HCID 86703232HCID 86703232, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 25 but 4-[2-bromo-5-(4-fluoro-2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-benzonitrile (Intermediate BJ) and 2,4-dimethoxypyrimidine-5-boronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine respectively. ESI-MS: tR=1.00 min, [M+H]+ 516 (LC-MS 1).

Sources & evidence

ORD record
ord-10b251258a6341ccb7814bb8bf9dd60a
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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