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

HRID 657793
Notes
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Reaction equation

HRID 657793 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 139377Methylboronic AcidHCID 250624105-Bromo-2-(4-((6-methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

Product 1

HCID 250223552-(4-((6-Methoxypyridin-3-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

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

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter cake was washed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative HPLC
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes