Water → HCID 21927804, compound

HRID 1508945Notes

Reaction equation

HRID 1508945 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:12][CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1.[OH2:24]>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[CH2:12][CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8]([CH3:9])(=[O:21])=[O:24])[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 2316404-Chloro-2-(methylsulfanyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Product 1

HCID 21927804HCID 21927804, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-2-(methylthio)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.208 g, 1.04 mmol) in methylene chloride (4 mL) was added m-CPBA (0.805 g, 4.66 mmol) in portions over a 15 min period at 0° C. and then the mixture was slowly warmed to rt and stirred overnight. After this time, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to afford the title compound (0.157 g, 75%). MW=232.69. 1H NMR (CDCl3, 300 MHz) δ 3.39-3.28 (m, 5H), 3.11 (t, J=7.6 Hz, 2H), 2.27 (t, J=7.6 Hz, 2H); APCI MS m/z 233 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-56f471d521b8498a8c6bdb6f7a8feb49
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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