Potassium Phosphate, Tribasic → 2-(4-((6-Methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

HRID 657793Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:29][CH2:28][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH:18][CH2:19][C:20]4[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:30]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:27][O:26][C:23]1[N:22]=[CH:21][C:20]([CH2:19][NH:18][C:17]2[C:12]3[CH2:11][N:10]([C:5]4[CH:4]=[CH:3][C:2]([CH3:30])=[CH:9][C:6]=4[C:7]#[N:8])[CH2:29][CH2:28][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-bromo-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile (55 mg, 0.12 mmol), methylboronic acid (18 mg, 0.30 mmol), potassium phosphate (90.6 mg, 0.427 mmol), tricyclohexylphosphine (6.8 mg, 0.024 mmol), toluene (3 mL), and water (0.2 mL) under argon was added palladium acetate (2.7 mg, 0.012 mmol). The mixture was heated at 100° C. for 3 h and then cooled to rt. The mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was concentrated and the residue was purified by preparative HPLC to yield an off-white solid.

Workup

temperaturecooled to rt
filtrationThe mixture was filtered through Celite
washthe filter cake was washed with EtOAc
concentrationThe filtrate was concentrated
customthe residue was purified by preparative HPLC
customto yield an off-white solid

Sources & evidence

ORD record: ord-07f7e12d479b4d25a58aab7a49ca9cce
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076345B2

Reaction notes

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