(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 86703185, compound

HRID 2204380Notes

Reaction equation

HRID 2204380 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:21](=[O:22])[C:20]3[CH:19]=[C:18](Br)[N:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[CH:15]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][O:35][C:36]1[N:41]=[C:40]([O:42][CH3:43])[C:39](B(O)O)=[CH:38][N:37]=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>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:21](=[O:22])[C:20]3[CH:19]=[C:18]([C:39]4[C:40]([O:42][CH3:43])=[N:41][C:36]([O:35][CH3:34])=[N:37][CH:38]=4)[N:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[CH:15]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 86703186HCID 86703186, compound

Product 1

HCID 86703185HCID 86703185, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 25 but 4-[2-bromo-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-4,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (Intermediate AI) 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 title compound was obtained as a white foam. tR=5.79 min (HPLC 4); ESI-MS: tR=1.26 min, [M+H]+ 596/598 (LC-MS 1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-3ce5b2430dbd45d4bee7c9fbb9b48a8c
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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