Dimethyl Sulfoxide → HCID 44820187, compound

HRID 2273991Notes

Reaction equation

HRID 2273991 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[O:12])=[CH:4][CH:3]=1.[NH2:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[NH2:25][C:26]1[N:31]=[C:30]([O:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=3[NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:15][CH:16]=2)[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 10796Cesium carbonateHCID 2233322-Amino-4-chloropyrimidineHCID 58533483HCID 58533483, compound

Product 1

HCID 44820187HCID 44820187, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide (157 mg, 486 μmol), 2-amino-4-chloropyrimidine (60 mg, 463 μmol), and cesium carbonate (302 mg, 926 μmol) in DMSO (2316 μl, 463 μmol) was placed in a microwave pressure vial, the vial was sealed, and the vial (reaction mixture) was heated in a Biotage Microwave to 150° C. for 12 minutes. LCMS analysis indicated that the reaction was complete. Reaction was diluted with EtOAc and washed with sat NaHCO3 (aq). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a brown color oil. The oil was taken up in minimal amount of DMSO and purified by Gilson HPLC {10-80% (0.1% TFA in CH3CN) in H2O over 20 min} to afford pure N-(4-(2-aminopyrimidin-4-yloxy)phenyl)-2-(4-fluorophenylamino)benzamide. MS Calcd for C23H18FN5O2=415. Found: [M+H]+=416.

Workup

  1. customthe vial was sealed
  2. customthe vial (reaction mixture)
  3. customReaction
  4. washwashed
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a brown color oil
  8. custompurified by Gilson HPLC {10-80% (0.1% TFA in CH3CN) in H2O over 20 min}

Sources & evidence

ORD record
ord-392fd6c3e4fd4a1da568c99fd9426fbb
Source dataset
uspto-grants-2015_09
Patent number
US09126935B2

Reaction notes

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