Water → HCID 58111406, compound

HRID 1429854Notes

Reaction equation

HRID 1429854 reaction equation
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:9]2[C:10](=[O:13])[C:11]=1I)[CH3:5])=[N+:2]=[N-:3].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C>[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:9]2[C:10](=[O:13])[C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:5])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58111416HCID 58111416, compound

Product 1

HCID 58111406HCID 58111406, compound

Reagents, catalysts & solvents 2

HCID 178482906HCID 178482906, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-(1-azidoethyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (100 mg, 0.28 mmol) and phenylboronic acid (48 mg, 0.39 mmol) in 1,4-dioxane (2 mL) was treated with sodium carbonate (45 mg, 0.42 mmol), water (0.50 mL), and dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (2.0 mg, 28 μmol), degassed with nitrogen for 5 minutes, and heated at 110° C. for 18 hours. The reaction mixture was purified by RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min). LCMS for C17H16N5O (M+H)+: m/z=306.1.

Workup

  1. customdegassed with nitrogen for 5 minutes
  2. customThe reaction mixture was purified by RP-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-f207295408aa42339957897ab62e93ff
Source dataset
uspto-grants-2015_01
Patent number
US08940752B2

Reaction notes

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