HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(6-Hydroxynaphthalen-2-yl)boronic acid → 2-(6-Hydroxynaphthalen-2-yl)pyrimidine-5-carboxylic acid

HRID 1771455
Notes
Print preview

Reaction equation

HRID 1771455 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5]2.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][N:17]=1>O1CCOCC1.O>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:16]1[N:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][N:17]=1)[CH:6]=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4349738(6-Hydroxynaphthalen-2-yl)boronic acidHCID 110949062-Chloropyrimidine-5-carboxylic acid

Product 1

HCID 1360695062-(6-Hydroxynaphthalen-2-yl)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

Followed procedure described in Step 1 of Example 7 starting from 6-hydroxynaphthalen-2-ylboronic acid and 2-chloropyrimidine-5-carboxylic acid with modifications: the solvent was dioxane/water (6/1), and the reaction was heated to 120° C. by microwave for 0.5 h. Purified by prep-HPLC. 1H-NMR (DMSO-d6 500 MHz): 13.70 (brs, 1H), 10.12 (s, 1H), 9.29 (s, 2H), 8.97 (s, 1H), 8.42-8.44 (d, J=9.0 Hz, 1H), 8.00-8.01 (d, J=8.5 Hz, 1H), 7.82-7.84 (d, J=9.0 Hz, 1H), 7.20 (s, 1H), 7.15-7.18 (dd, J=2.0, 9.0 Hz, 2H). MS (ESI): m/z=267.0 [M+1]+.

Workup

  1. customPurified by prep-HPLC

Sources & evidence

ORD record
ord-a9da953bdfcb4fc0bd77fa3b0f73f4a6
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249132B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes