Potassium Carbonate → HCID 16123061, compound

HRID 1893903Notes

Reaction equation

HRID 1893903 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([CH:14]([CH3:16])[CH3:15])[C:6]=2[N:7]=1.[NH:18]1[CH:22]=[CH:21][C:20](B(O)O)=[N:19]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10]([C:20]3[NH:19][N:18]=[CH:22][CH:21]=3)[C:9](=[O:13])[N:8]([CH:14]([CH3:16])[CH3:15])[C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 57606978HCID 57606978, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 16123061HCID 16123061, compoundYield 13.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 350 mL pressure tube 2-amino-6-bromo-8-isopropyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (1.50 g, 5.05 mmol), 1H-pyrazol-3-yl boronic acid (1.12 g, 10.09 mmol), K2CO3 (336 mg, 15.1 mmol), and tetrakis(triphenylphosphine) palladium (0) (583 mg, 0.0504 mmol) were dissolved in 50 mL dioxane and 5 mL H2O. The tube was sealed, heated to 100° C. and allowed to react overnight. A color change was observed. LCMS indicated no presence of starting material. Sample was filtered through a syringe filter and evaporated to dryness. Compound was dissolved in ethyl acetate and triturated in hexane. Light yellow powder of 2-amino-8-isopropyl-4-methyl-6-(1H-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (195 mg, 13.7% yield) was found to be 98% pure by HPLC. NMR (400 MHz, CDCl3) δ 12.97 (br s, 1H), 8.35 (s, 1H), 7.60 (br s, 1H), 7.21 (s, 2H), 6.94 (s, 1H), 5.86 (br s, 1H), 2.50 (m, 6H), 1.54 (s, 3H), MS (EI) for C14H16N6O: 285.0 (MH+).

Workup

  1. customThe tube was sealed
  2. customto react overnight
  3. filtrationSample was filtered through a syringe
  4. filtrationfilter
  5. customevaporated to dryness
  6. dissolutionCompound was dissolved in ethyl acetate
  7. customtriturated in hexane

Sources & evidence

ORD record
ord-fabc6d49ce594eadb8a7cca14323448f
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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