Potassium Phosphate, Tribasic → HCID 67298135, compound

HRID 1520383Notes

Reaction equation

HRID 1520383 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:18][CH3:19])=[N:7][C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9]2)=[CH:4][C:3]=1[CH3:20].[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[ClH:1].[ClH:1].[F:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([NH:18][CH3:19])=[N:7][C:8]([C:12]4[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=4)=[N:9]3)=[CH:4][C:3]=2[CH3:20])[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27339863-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 67298413HCID 67298413, compound

Product 1

HCID 67298135HCID 67298135, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-chloro-N,6-dimethyl-2-(pyridin-3-yl)quinazolin-4-amine (400 mg, 1.40 mmol), 3-fluorophenylboronic acid (294 g, 2.10 mmol), Pd(OAc) (15.8 mg, 0.070 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86.7 mg, 0.211 mmol), K3PO4 (900 mg, 4.23 mmol) in dioxane (10 mL) and water (2 mL) was stirred under reflux for 2.5 h. Ethyl acetate (20 mL) was added to the cooled mixture and a precipiate formed and was filtered. The solid was recrystallized from DMF and water to give the title compound as free form. The solid was suspended in ethyl acetate (10 mL) and 4N HCl in ethyl acetate (1.0 mL) was added. The resulting solid was subjected to sonication for 20 min, filtered and dried to give the title compound as the bis-110 salt (0.10 g, 18.7%).

Workup

  1. temperatureunder reflux for 2.5 h
  2. customa precipiate formed
  3. filtrationwas filtered
  4. customThe solid was recrystallized from DMF and water

Sources & evidence

ORD record
ord-65ad70be005640df921cb871e6daa32d
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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