m-Chloroperbenzoic acid → HCID 178518414, compound

HRID 750803Notes

Reaction equation

HRID 750803 reaction equation
CS[C:3]1[N:8]=[C:7]([OH:9])[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:4]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[OH:33][C:3]1[N:8]=[C:7]([OH:9])[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178503528HCID 178503528, compound

Product 1

HCID 178518414HCID 178518414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 mL round bottom flask fitted with a magnetic stirrer bar was added 2-methylthio-4-hydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine from Example 11 (40 mg, 0.1 mmol) and 1.0 mL DCM. The reaction flask was cooled in an ice bath and mCPBA (70%, 50mg, 0.22 mmol) was added all at once. After 2 h, two new products were observed by LC. The product eluting at Rt=3.38 min was 2-methylsulfonyl-4-hydroxy-5-(4-chlorophenyl)-6-(2, 4-dichlorophenyl)pyrimidine, m/e=431 (M++1) and that at Rt=2.91 min is 2,4-dihydroxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine: m/e=367 (M+). The mixture was poured into 2 N NaOH and heated briefly. The precipitate that formed was filtered, washed with water and dried under reduced pressure. The title product was recovered. m/e=367 (M+). Rt=2.91 min; 1H-NMR 500 MHz (CDCl3): δ 6.98 (d, J=8 Hz, 2H), 7.08 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 3H), 7.38 (d, J=2 Hz, 1H), 9.8 (bs, 1H), 10.1 (bs 1H).

Workup

  1. customTo a 10 mL round bottom flask fitted with a magnetic stirrer bar
  2. temperatureThe reaction flask was cooled in an ice bath
  3. washThe product eluting at Rt=3.38 min
  4. additionThe mixture was poured into 2 N NaOH
  5. temperatureheated briefly
  6. customThe precipitate that formed
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried under reduced pressure
  10. customThe title product was recovered

Sources & evidence

ORD record
ord-f647e3f6c6694296bb22c99bf368ad78
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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