Water → 2-Methylthio-4-(2-piperidin-1-yl-ethoxy)-6-(3-trifluoromethyl-phenyl)-pyrimidine

HRID 2053101Notes

Reaction equation

[H-].[Na+].Cl[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:7]=[C:6]([S:20][CH3:21])[N:5]=1.[OH:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>C1COCC1.C(OC)(C)(C)C>[CH3:21][S:20][C:6]1[N:5]=[C:4]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (30 mg, 1.23 mmol) was added to a mixture of 4-chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine (187 mg, 0.62 mmol) and 1-(2-hydroxyethyl)piperidine (120 μl, 0.92 mmol) in dry THF (6 ml). The mixture was heated at 40° C. for 2 h. After cooling, water and tert-butyl-methyl ether were added. The aqueous layer was extracted twice with tBuOMe. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 95/5) to yield the above titled compound: 190 mg (yield: 78%).

Workup

temperatureAfter cooling
extractionThe aqueous layer was extracted twice with tBuOMe
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was chromatographed over silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record: ord-7f278a00648e4f2987aa754ba2a0472d
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326715B2

Reaction notes

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