Water → HCID 11336608, compound

HRID 898131Notes

Reaction equation

[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[C:10]([CH3:16])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[NH:19]1.C([BH3-])#N.[Na+].O>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CC(O)C>[CH3:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[N:19]1[CH2:14][C:12]1[CH:11]=[C:10]([CH3:16])[N:9]=[C:8]([S:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[N:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2-Hexylsulfanyl-6-methyl-pyrimidine-4-carbaldehyde (0.2 g, 1 mmol) and 2,6-dimethylpiperidine (0.23 mL, 2 mmol) were dissolved in tetraisopropyl orthotitanate (0.5 mL) and stirred at 20° C. for 1 h. The solution was diluted with 2-propanol (5 mL) and treated with sodium cyanoborohydride (105 mg, 2 mmol) at 20° C. for 20 h. Water (1 mL) was added, and the resulting precipitate filtered off and evaporated. The product was extracted with AcOEt, sat. NH4Cl solution, dried and concentrated. The residue was purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD, S-5 μM, 12 nm) with an acetonitrile-water gradient. One obtained 37 mg (36%) of a colorless liquid. MS: m/z=336 (M+H).

Workup

filtrationthe resulting precipitate filtered off
customevaporated
extractionThe product was extracted with AcOEt, sat. NH4Cl solution
customdried
concentrationconcentrated
customThe residue was purified by preparative HPLC chromatography on a YMC combiprep ODS-AQ column (75×20 mm iD

Sources & evidence

ORD record: ord-d79c7950f52947e0bbe5d0238828362c
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351700B2

Reaction notes

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