Phenylboronic Acid → HCID 28799520, compound

HRID 254181Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of methyl 2-amino-6-chloropyrimidine-4-carboxylate (0.2 g, 1.07 mmol) and phenylboronic acid (0.16 g, 1.3 mmol) in THF (10 mL) was treated with saturated aqueous NaHCO3 (1.6 mL). Nitrogen was bubbled through the solution for 5 min then tetrakis(triphenylphosphine)palladium(0) (0.04 g) was added and the mixture refluxed under nitrogen overnight. The mixture was treated with aqueous LiOH (1-M, 1 mL), heated at 90° C. for 2 h, concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous layer was acidified to pH 1 with 2-N HCl, the resulting suspension centrifuged, the liquors decanted and the resulting solid dried to give the title compound (0.17 g, 72%) as a white powder which was used directly in the next step without further purification; M/Z 216 (M+H)+; retention time 1.60 min (Method AM).

Workup

customNitrogen was bubbled through the solution for 5 min
additiontetrakis(triphenylphosphine)palladium(0) (0.04 g) was added
temperaturethe mixture refluxed under nitrogen overnight
additionThe mixture was treated with aqueous LiOH (1-M, 1 mL)
concentrationconcentrated in vacuo
custompartitioned between ethyl acetate and water
customthe liquors decanted
customthe resulting solid dried

Sources & evidence

ORD record: ord-bd6618b5cde74a8da7b403db0ef62d52
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875600B2

Reaction notes

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