m-Chloroperbenzoic acid → HCID 19781652, compound

HRID 257793Notes

Reaction equation

HRID 257793 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:10]2=[O:27])[CH:6]=[CH:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[N:11]([CH2:20][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:10]2=[O:27])[CH:6]=[CH:7][CH:8]=1)=[O:33]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19781593HCID 19781593, compound

Product 1

HCID 19781652HCID 19781652, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Methylthiophenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (100 mg, 0.27 mmole), prepared, e.g., as described in Example 5B, was dissolved in methylene chloride (20 ml) and cooled to 0° C. m-Chloroperoxybenzoic acid (45 mg, 0.27 mmole) was added to the solution. The solution was stirred for 2 hours at 0° C. The solution was then washed with a 10% solution of Na2SO3 (2 ml) followed by a wash with saturated NaHCO3 (10 ml). The organic and aqueous phases were separated and the organic phase was dried with MgSO4. The solvents were removed and the residue purified by preparative thin-layer chromatography (ethyl acetate as eluent) yielding 51 mg (0.13 mmole, 48% yield) of 1-(3-methylsulfinylphenyl)-3-(4-pyridylmethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, as a white solid, (mp 218°-219° C.).

Workup

  1. additionwas added to the solution
  2. washThe solution was then washed with a 10% solution of Na2SO3 (2 ml)
  3. washa wash with saturated NaHCO3 (10 ml)
  4. customThe organic and aqueous phases were separated
  5. dry with materialthe organic phase was dried with MgSO4
  6. customThe solvents were removed
  7. customthe residue purified by preparative thin-layer chromatography (ethyl acetate as eluent)

Sources & evidence

ORD record
ord-53c17e47116646c5be4982b8f2adc02c
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

Loading…