Hydrochloric Acid → HCID 86710177, compound

HRID 2284409Notes

Reaction equation

HRID 2284409 reaction equation
Br[C:2]1[CH:11]=[N:10][C:9]2[C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:7][C:6]([Cl:18])=[N:5][C:4]=2[CH:3]=1.[C:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([OH:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(O)C>[Cl:18][C:6]1[N:7]=[C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[N:10]=[CH:11][C:2]([C:25]3[CH:26]=[CH:27][C:22]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=3)=[CH:3][C:4]=2[N:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 86665768HCID 86665768, compound

Product 1

HCID 86710177HCID 86710177, compoundYield 71.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a 50 mL round bottom flask, 4-(7-bromo-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine (1.0 g, 0.0030 mol—Preparation 3), 4-carboxyphenylboronic acid (0.5 g, 0.0030 mol), sodium carbonate (0.64 g, 0.0060 mol) dioxane (60 mL), ethanol (10 mL) and water (10 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)2Cl2 (0.106 g, 0.00015 mol) was added and degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 90° C. for 2 hours. The volatiles were evaporated to provide a residue. The residue was stirred with water and acidified with 2 N hydrochloric acid to pH 5-6 to provide a precipitate. The precipitate was collected by filtration and dried under reduced pressure to afford the title compound (0.8 g, 71%). The compound was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6): δ 9.18 (d, J=2.4 Hz, 1H), 8.40 (d, J=2.4 Hz, 1H), 8.10-8.03 (m, 4H), 4.58 (br s, 4H), 3.79 (t, J=4.5 Hz, 4H): LC-MS (ESI): Calculated mass: 370.0; Observed mass [M+H]+: 371.1 (RT=1.37 min).

Workup

  1. customThe reaction mixture was degassed with N2 for 5-10 minutes
  2. customdegassed with N2 for 5-10 minutes
  3. customThe volatiles were evaporated
  4. customto provide a residue
  5. customto provide a precipitate
  6. filtrationThe precipitate was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-460391b0d83b41b081ff7e57a66c7fbc
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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