m-Chloroperbenzoic acid → 4'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

HRID 1397136Notes

Reaction equation

HRID 1397136 reaction equation
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:27])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 679837614'-(Cyclopropylmethyl)-2-(methylsulfanyl)-4,5'-bipyrimidine

Product 1

HCID 679831774'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4′-(cyclopropylmethyl)-2-(methylsulfanyl)-4,5′-bipyrimidine (4a) (62.5 mg, 0.242 mmol) in DCM (968 μl), mCPBA (65.1 mg, 0.290 mmol) was added and the reaction mixture was stirred at rt for 1 hour. The crude reaction mixture was partitioned between saturated sodium bicarbonate solution and DCM. The aqueous layer was separated and back-extracted twice with DCM. The combined organic extracts were washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was carried on to the next step without further purification. MS (ES+): m/z=275.2 (100) [MH+]. HPLC: tR=0.72 minute over 3 minutes. Purity: 100% [HPLC (LC/MS) at 220 nm].

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between saturated sodium bicarbonate solution and DCM
  3. customThe aqueous layer was separated
  4. extractionback-extracted twice with DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was carried on to the next step without further purification
  9. waitHPLC: tR=0.72 minute over 3 minutes

Sources & evidence

ORD record
ord-354d53a64e894d7b920454679594783d
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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