Sodium Carbonate → HCID 68108965, compound

HRID 1023311Notes

Reaction equation

HRID 1023311 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]2[C:8](=[O:17])[N:7]([CH3:18])[CH:6]=[N:5][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[CH:29][C:30]3[O:34][CH:33]=[N:32][C:31]=3[CH:35]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:34]1[C:30]2[CH:29]=[CH:28][C:27]([C:2]3[N:11]=[C:10]([NH:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]4[C:8](=[O:17])[N:7]([CH3:18])[CH:6]=[N:5][C:4]=4[CH:3]=3)=[CH:35][C:31]=2[N:32]=[CH:33]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 532168175-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazoleHCID 86667982HCID 86667982, compound

Product 1

HCID 68108965HCID 68108965, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 7-chloro-5-(2-methoxyethylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (15.0 mg, 0.0559 mmol) in 1,4-dioxane (0.5 mL) were added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (15.0 mg, 0.0612 mmol), 2M aqueous Na2CO3 solution (83.7 μL, 0.167 mmol), and a catalytic amount of Pd(PPh3)4. The reaction mixture was purged with N2 and heated at 140° C. by a microwave reactor for 15 minutes. The mixture was then cooled, quenched with H2O (5 mL) and extracted with ethyl acetate (3×2.5 mL). The combined organic layers were evaporated under vacuum and the residue was purified by preparatory LC/MS to provide 7-(benzo[d]oxazol-5-yl)-5-(2-methoxyethylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one, which was completely decomposed to the title compound at room temperature; HPLC-MS calculated for C18H19N5O4 (M+H+) 370.1, found 370.1.

Workup

  1. customThe reaction mixture was purged with N2
  2. temperatureThe mixture was then cooled
  3. customquenched with H2O (5 mL)
  4. extractionextracted with ethyl acetate (3×2.5 mL)
  5. customThe combined organic layers were evaporated under vacuum
  6. customthe residue was purified by preparatory LC/MS

Sources & evidence

ORD record
ord-59cd0bf7410e41cc865bb534cf552130
Source dataset
uspto-grants-2014_05
Patent number
US08722692B2

Reaction notes

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