3-(1,3,2-Dioxaborinan-2-yl)pyridine → 4-(5-Pyridin-3-ylpyrimidin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

HRID 393720Notes

Reaction equation

HRID 393720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=C[C:23](F)=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC([N:34]1CCN(C2N=CC(Br)=CN=2)CC1)=O)(C)(C)C.B1(C2C=CC=NC=2)OCCCO1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]3[CH:25]=[N:34][CH:23]=[CH:22][CH:21]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21914476tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylateHCID 69850026Tert-butyl 4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylate

Product 1

HCID 698949874-(5-Pyridin-3-ylpyrimidin-2-yl)piperazine-1-carboxylic acid tert-butyl esterYield 99%

Procedure

Prepared according to the method for the preparation of 4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl ester, from 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (0.403 g) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.211 g), to yield the title compound as an orange solid (0.399 g, 99%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ba4d2f23235b412f94001f315bb331a1
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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