1-Cyclohexenylboronic acid → HCID 178457450, compound

HRID 2169227Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]([CH:30]([CH3:32])[CH3:31])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2Br)[N:8]=1)=[O:6].[C:33]1(B(O)O)[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1.C(OC(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2C=C(OC)C=CC=2C2C=CC=CC=2)N=1)=O)(C)(C)C>>[OH:1][CH2:2][CH2:3][N:4]([CH:30]([CH3:32])[CH3:31])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[N:8]=1)=[O:6]

Participants

Reactant 3

HCID 38629021-Cyclohexenylboronic acid

HCID 178457447HCID 178457447, compound

HCID 178488539HCID 178488539, compound

Product 1

HCID 178457450HCID 178457450, compoundYield 41.9%

Procedure

5-Benzyloxy-2-(2-cyclohex-1-enyl-benzyl)-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (155) (210 mg, 41.9%) as a colorless sticky liquid was synthesized from 5-benzyloxy-2-(2-bromobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (151) (500 mg, 0.999 mmol) and cyclohexene boronic acid (188.84 mg, 1.49 mmol) following the procedure as described for 5-benzyloxy-6-hydroxy-2-(4-methoxy-biphenyl-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (139).

Sources & evidence

ORD record: ord-77ff1e2be2504d43b083653de8ad3919
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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