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Triphenylphosphine → HCID 11385276, compound

HRID 2216314
Notes
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Reaction equation

HRID 2216314 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:40]1[CH:41]=[N:42][CH:43]=[N:44][CH:45]=1)CCC.[Li+].[Cl-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:40]3[CH:41]=[N:42][CH:43]=[N:44][CH:45]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 27632495-(Tributylstannyl)pyrimidineHCID 86595018HCID 86595018, compound

Product 1

HCID 11385276HCID 11385276, compound
Yield 82.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (95 mg, 0.18 mmol), prepared by the method described in Example 22, 5-tributylstannanyl-pyrimidine (75 mg, 0.20 mmol), LiCl (23 mg, 0.55 mmol) and DMF (4 mL) was deoxygenated with N2 for 10 min, and then Pd(PPh3)2Cl2 (13 mg, 0.018 mmol) and PPh3 (10 mg, 0.036 mmol) were added. The mixture was heated at 150° C. under N2 for 2 h and then cooled to room temperature. Saturated aqueous KF was added, and the mixture was extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc) to provide the target compound (66 mg, 80%) as a white solid: mp 210–212° C.; 1H NMR (300 MHz, CDCl3) δ 9.29 (s, 1H), 8.96 (s, 1H), 8.80 (s, 1H), 8.30 (br s, 1H), 8.13 (d, J=8.5 Hz, 2H), 7.76 (d, J=8.5 Hz, 2H), 6.93 (s, 2H), 2.41 (s, 3H), 2.31 (s, 3H), 2.03 (s, 6H); APCI MS m/z 446 [(M+H)+, calcd for C24H24N5O2S, 446.2].

Workup

  1. customprepared by the method
  2. customwas deoxygenated with N2 for 10 min
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted three times with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc)

Sources & evidence

ORD record
ord-a25509b4bad04543981001713937ec75
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07112585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes