m-Chloroperbenzoic acid → 4-(2-(4-aminophenylsulfinyl)pyridin-3-yl)-N-methylpyrimidin-2-amine

HRID 1361630Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>ClCCl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:28])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) suspension of 4-(2-(4-aminophenylthio)pyridin-3-yl)-N-methylpyrimidin-2-amine (400 mg, 1.28 mmol) in 20 mL of dichloromethane was added dropwise a solution of 3-chloroperoxybenzoic acid (330 mg, 1.28 mmol, 77% maximum purity) in dichloromethane. The reaction was stirred for 7 hours at 0° C. Then the reaction flask was stored in the freezer overnight without stirring. After 17 hours, the reaction was removed from the freezer and was stirred for another 6 hours in an ice-water bath. The solid was filtered off and collected. The product, 4-(2-(4-aminophenylsulfinyl)pyridin-3-yl)-N-methylpyrimidin-2-amine was obtained as an off-white solid. 1H NMR (Varian, 300 MHz, CDCl3): 8.76 (s, 1H), 8.35 (s, 1H), 8.00 (d, J=7.7 Hz, 1H), 7.60 (m, 1H), 7.46 (m, 3H), 6.78 (d, J=4.9 Hz, 1H), 6.46 (d, J=8.0 Hz, 2H), 5.63 (br s, 2H), 2.81 (s, 3H).

Workup

customwas stored in the freezer overnight
stirringwithout stirring
waitAfter 17 hours
customthe reaction was removed from the freezer
stirringwas stirred for another 6 hours in an ice-water bath
filtrationThe solid was filtered off
customcollected

Sources & evidence

ORD record: ord-79de000796254181bf85e198d75dc233
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880000B2

Reaction notes

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