Potassium Carbonate → HCID 178488427, compound

HRID 641664Notes

Reaction equation

HRID 641664 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][N:31]=1>[Pd](Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[CH:11]=[C:10]([C:33]3[CH:32]=[N:31][C:30]([O:29][CH3:28])=[CH:35][CH:34]=3)[C:9](=[O:13])[N:8]([C@H:14]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 178433331HCID 178433331, compound

Product 1

HCID 178488427HCID 178488427, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
100 °C

Procedure

A flask containing 2-amino-6-bromo-8-(trans-4-hydroxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (105 mg, 0.297 mmol), potassium carbonate (123 mg, 0.892 mmol), and 2-methoxy-5-pyridine boronic acid (52 mg, 0.34 mmol) was evacuated and back-filled with nitrogen (2×). A solution of 5:1 dimethylformade:water (1.8 mL) was bubbled with argon for 15 min then added to the flask followed by bis(tripehnylphosphine) palladium (II) chloride (10 mg, 0.015 mmol). The flask was fitted with a cold finger, evacuated and back filled with nitrogen (2×) then heated to 100° C. for 4 hr. The mixture was cooled overnight, diluted with methanol and chloroform then filtered through a glass fiber filter to filter out palladium. The filtrate was concentrated and the residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-6%) to afford the title compound (80, 71%).

Workup

  1. customwas evacuated
  2. additionback-filled with nitrogen (2×)
  3. customA solution of 5:1 dimethylformade:water (1.8 mL) was bubbled with argon for 15 min
  4. additionthen added to the flask
  5. customThe flask was fitted with a cold finger
  6. customevacuated
  7. additionback filled with nitrogen (2×)
  8. temperatureThe mixture was cooled overnight
  9. additiondiluted with methanol and chloroform
  10. filtrationthen filtered through a glass fiber
  11. filtrationfilter
  12. filtrationto filter out palladium
  13. concentrationThe filtrate was concentrated
  14. customthe residue was purified by flash chromatography
  15. washeluting with chloroform/7 N ammonia in methanol (0.5-6%)

Sources & evidence

ORD record
ord-bdf19614a87c4124a4e96d85f1f58535
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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