Potassium Carbonate → HCID 57833250, compound

HRID 729928Notes

Reaction equation

HRID 729928 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:19]=[C:18]([NH2:28])[N:17]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB(/[CH:43]=[CH:44]/[CH2:45][CH2:46][OH:47])O1>CC(N(C)C)=O>[NH2:28][C:18]1[N:17]=[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2](/[CH:43]=[CH:44]/[CH2:45][CH2:46][OH:47])[CH:7]=3)=[CH:10][CH:11]=2)[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57416199(3E)-4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-olHCID 57833225HCID 57833225, compound

Product 1

HCID 57833250HCID 57833250, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

N4-{4-[(2-chloropyridin-4-yl)oxy]phenyl}-6-phenylpyrimidine-2,4-diamine (0.10 g, 0.26 mmol, Example 48), K2CO3 (0.089 g, 0.64 mmol), and DMA (2.5 mL) were placed into a small microwave vial. The mixture was degassed for 10 min before (3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-ol (0.10 g, 0.33 mmol) and Pd(dppf)Cl2 CH2Cl2 complex (0.012 g, 0.020 mmol) were added. The mixture was heated at 150° C. for 20 min in a microwave reactor. The mixture was cooled, filtered, and purified by prep-HPLC. Concentration of the desired fractions gave 0.016 g of the title compound (10%).

Workup

  1. additionwere added
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-dc4828f9943048a29145c933dced0ad2
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

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