Potassium Phosphate, Tribasic → HCID 66718415, compound

HRID 2096673Notes

Reaction equation

Cl[C:2]1[C:3]2[NH:10][N:9]([NH2:11])[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4([OH:25])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[N:14]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[OH:25][C:19]1([C:15]2[N:14]=[C:13]([CH2:12][N:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:3]=4[NH:10][N:9]3[NH2:11])[CH:18]=[CH:17][CH:16]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of the 7-chloro-3-(6-[4-hydroxytetrahydropyran-4-yl]pyridine-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-2-amine (0.10 g, 0.27 mmol) and phenylboronic acid (0.05 g, 0.41 mmol) and potassium phosphate (0.12 g, 0.55 mmol) in 1,4-dioxane (5 mL) was degassed by sparging with nitrogen. Tetrakis triphenylphosphine palladium (16 mg) was then added, the solution degassed again and the resultant mixture heated at 100° C. for seven hours. The mixture was then concentrated onto Isolute-HM in vacuo, purified by column chromatography (silica, eluting with 3:1 ethyl acetate:hexane and neat ethyl acetate) and triturated with diethyl ether to give the title compound (41 mg, 37%) as a pale beige solid.

Workup

customby sparging with nitrogen
additionTetrakis triphenylphosphine palladium (16 mg) was then added
customthe solution degassed again
concentrationThe mixture was then concentrated onto Isolute-HM in vacuo
custompurified by column chromatography (silica, eluting with 3:1 ethyl acetate:hexane and neat ethyl acetate)
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-0d96c902474e4117a6039673931cc5cc
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450328B2

Reaction notes

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