Morpholine → 4-[1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethyl]-morpholine

HRID 898135Notes

Reaction equation

[CH2:1]([S:7][C:8]1[N:13]=[C:12]([C:14](=O)[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CC(O)C>[CH2:1]([S:7][C:8]1[N:13]=[C:12]([CH:14]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH3:15])[CH:11]=[C:10]([CH3:17])[N:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone (200 mg, 0.79 mmol) and morpholine (138 μL, 1.58 mol) were dissolved in tetraisopropyl orthotitanate (0.5 mL) and heated at 80° C. for 16 h. The brown solution was diluted with 2-propanol (5 mL) and treated with sodium cyanoborohydride (32 mg, 0.5 mmol) at 20° C. for 6 h. Extraction: 2×AcOEt, 2× sat. NH4Cl solution. Chromatography: Si-amine, heptane/ethyl acetate 85:15. One obtained 86 mg (34%) of a yellow oil. MS: m/z=324 (M+H).

Workup

extractionExtraction

Sources & evidence

ORD record: ord-ab5171619d60457e82aa081470e960ae
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351700B2

Reaction notes

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