Sodium Carbonate → HCID 68274328, compound

HRID 629026Notes

Reaction equation

HRID 629026 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:10]([S:11][CH3:12])=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:8]=[C:7](Cl)[N:6]=1.CC1(C)C(C)(C)OB([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:10]([S:11][CH3:12])=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:8]=[C:7]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86673508HCID 86673508, compound

Product 1

HCID 68274328HCID 68274328, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-4-yl)-acetic acid methyl ester (420 mg, 1.47 mmol.), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-aniline) (357 mg, 1.62 mmol.), (PPh3)4Pd (170 mg, 0.07 mmol.), 2M Na2CO3 (2.2 ml, 4.14 mmol, 3.0 eq.) and dioxane (10 ml) was added a reaction vessel which was flushed with argon. The reaction mixture was stirred at 90° C. for 12 hr then dried, and the solvent was evaporated. The reaction mixture was partitioned between EA and water, the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 3:2) to give a pale yellow solid of 424 mg (43.8%).

Workup

  1. additionwas added a reaction vessel which
  2. customwas flushed with argon
  3. customthen dried
  4. customthe solvent was evaporated
  5. customThe reaction mixture was partitioned between EA and water
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 3:2)
  11. customto give a pale yellow solid of 424 mg (43.8%)

Sources & evidence

ORD record
ord-a6578cdee2cb406a83d431b8b978ef97
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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