(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 72204205, compound

HRID 2204366Notes

Reaction equation

HRID 2204366 reaction equation
Br[C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:10]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])[C:11](=[O:12])[C:4]=2[CH:3]=1.[CH3:28][O:29][C:30]1[N:35]=[C:34]([O:36][CH3:37])[C:33](B(O)O)=[CH:32][N:31]=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>>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([CH3:20])=[C:13]([N:10]2[C:11](=[O:12])[C:4]3[CH:3]=[C:2]([C:33]4[C:34]([O:36][CH3:37])=[N:35][C:30]([O:29][CH3:28])=[N:31][CH:32]=4)[N:6]([CH2:7][CH3:8])[C:5]=3[CH:9]2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:18]=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 86703114HCID 86703114, compound2×HCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Product 1

HCID 72204205HCID 72204205, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 25 but 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate K) 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. The product was purified by flash chromatography to afford the title compound as a white solid. tR: 5.69 min (HPLC 4); ESI-MS: tR=1.30 min, [M+H]+ 523/525 (LC-MS 1); 1H-NMR (d6-DMSO, 600 MHz, 100° C.): (rotamers) 8.31 (s, 1H), 7.40 (m, 2H), 7.30 (m, 1H), 7.26 (m, 2H), 7.15-7.23 (m, 2H), 6.37 (s, 1H), 6.29 (s, 1H), 4.00 (s, 3H), 3.97 (s, 3H), 3.38/3.59 (m, 2H), 2.07 (s, 3H), 0.86 (m, 3H).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-76b951e86d7f4c8bbcd87f917569fad8
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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