Water → HCID 18186505, compound

HRID 1357545Notes

Reaction equation

HRID 1357545 reaction equation
[NH:1]([C:8]1[C:13](I)=[CH:12][N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH:1]([C:8]1[C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][N:11]=[C:10]([Cl:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7501StyreneHCID 8471TriethylamineHCID 18186468HCID 18186468, compound

Product 1

HCID 18186505HCID 18186505, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-anilino-2-chloro-5-iodopyrimidine (Method 59, 331 mg, 1 mmol), styrene (130 mg, 1.2 mmol), triethylamine (0.5 ml) and palladium acetate (20 mg) in acetonitrile (10 ml) was heated at 80° C. for 20 hours. The solution was poured into water (100 ml) and the mixture was extracted with ethyl acetate (2×50 ml). The extracts were washed with water (2×50 ml) and saturated sodium chloride (50 ml) and dried. Volatile material was removed by evaporation and the residue was purified by bond elute chromatography, eluting with 10% ethyl acetate in isohexane, to give the product (40 mg). NMR (CDCl3): 6.8 (d, 1H), 7.0 (d, 2H), 7.15 (t, 1H), 7.3-7.45 (m, 5H), 7.5 (d, 2H), 7.6 (d, 2H), 8.2 (s, 1H); MS (MH+): 308, 310.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  2. washThe extracts were washed with water (2×50 ml) and saturated sodium chloride (50 ml)
  3. customdried
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by bond
  6. washelute chromatography
  7. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f4637199469640b28ebacbe57f5e69d5
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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