Triphenylphosphine → HCID 18327493, compound

HRID 1004044Notes

Reaction equation

HRID 1004044 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([S:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].NC1C=C(Cl)C(O)=C(Cl)C=1.ClC1N=C(SC2C=C(C)C=C(C)C=2)C=CN=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:72][CH2:73][N:74]1[CH2:78][CH2:77][CH2:76][CH2:75]1>O1CCCC1>[Cl:9][C:6]1[CH:5]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([S:17][C:18]3[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=3)[CH:14]=[CH:13][N:12]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][CH2:72][CH2:73][N:74]1[CH2:78][CH2:77][CH2:76][CH2:75]1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 800374-Amino-2,6-dichlorophenolHCID 18327465HCID 18327465, compoundHCID 18327474HCID 18327474, compound

Product 1

HCID 18327493HCID 18327493, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3,5-dichloro-4-hydroxyphenyl)-4-(3,5-dimethylphenylsulphanyl)-2-pyrimidineamine (1.0 g, 2.55 mmol--prepared from 4-amino-2,6-dichlorophenol and 2-chloro-4-(3,5-dimethylphenylsulphanyl)-pyrimidine according to the method of Example 4) in dry tetrahydrofuran were added triphenylphosphine (802 mg, 3.06 mmol) and N-(2-hydroxyethyl)pyrrolidine (0.3 ml, 2.55 mmol), followed by diethyl azadicarboxylate (0.49 ml, 3.1 mmol). The resulting solution was heated at reflux for 18 h and on cooling the reaction was partitioned between ethyl acetate (200 ml) and saturated aqueous NaHCO3 (200 ml). The organic phase was dried (MgSO4), evaporated and the residue columned (silica;ethyl acetate) to give the title compound (400 mg) as a white foam. δH 8.08 (1H, d, J 5.8 Hz), 7.56 92H, s), 7.17 (2H, s), 7.09 (1H, s), 7.05 (1H, s), 6.28 (1H, d, J 5.8 Hz), 4.18 (2H, t, J 8.6 Hz), 2.59 (2H, t, J 8.6 Hz), 2.59 (2H, t, J 8.6 Hz), 2.69 (4H, m), 2.31 (6H, s) and 1.80 (4H, m). MS m/z 489.2/490.9 (MH+).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 h
  3. temperatureon cooling the reaction
  4. customwas partitioned between ethyl acetate (200 ml) and saturated aqueous NaHCO3 (200 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-9ad70e7887fc465da7dc4365c059de8f
Source dataset
uspto-grants-2000_04
Patent number
US06048866

Reaction notes

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