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

HRID 2359739Notes

Reaction equation

HRID 2359739 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-c440c348a5b944029944a4ae20b85ca1
Source dataset
uspto-grants-2014_04
Patent number
US08685993B2

Reaction notes

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