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

HRID 1397142Notes

Reaction equation

HRID 1397142 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]=[C:7]([NH2:19])[N:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl.O>[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:28])[N:12]=3)=[CH:9][N:8]=[C:7]([NH2:19])[N:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 679837974'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-amine

Product 1

HCID 679839214'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4′-(cyclopropylmethyl)-2-(methylthio)-4,5′-bipyrimidin-2′-amine (4a) (2.17 g, 7.14 mmol) in DCM (14.29 ml) was added m-CPBA (1.761 g, 7.14 mmol). Immediately after the addition of m-CPBA, the reaction completion was observed. The reaction mixture was diluted with DCM and water. The organic layer was washed with saturated sodium bicarbonate and brine, dried with sodium sulfate, and concentrated in vacuo. The crude residue was purified by Biotage flash chromatography [100 g SNAP column, eluted with 1-15% MeOH/DCM] to obtain the desired product as a slightly pale yellow solid (1.47 g, 71% yield). MS (ES+): m/z=290.4/291.5 (100/10) [MH+]. HPLC: tR=0.76 min over 3 min. Purity: 100% [HPLC (LC/MS) at 220 nm].

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate and brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by Biotage flash chromatography [100 g SNAP column, eluted with 1-15% MeOH/DCM]

Sources & evidence

ORD record
ord-5bdd64bf9ec54ef28f5585d29b99f544
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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