Diisopropylethylamine → HCID 118162128, compound

HRID 1749514Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[NH2:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[C:15]([CH3:21])([CH3:20])[CH2:14]1.CCN(C(C)C)C(C)C>C(O)(C)C>[OH:19][C@H:16]1[CH2:17][CH2:18][C@@H:13]([NH:12][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)[CH2:14][C:15]1([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (2.15 g, 11.6 mmol)), (1S,4R)-4-amino-2,2-dimethylcyclohexanol (1.51 g, 10.5 mmol) and DIEA (2.72 g, 21.1 mmol) in isopropanol (30 mL) was heated at 100° C. for 3 h. After removal of the organic solvent under reduced pressure, the residue was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give a crude product, which was purified by silica gel column chromatography (15% ethyl acetate in petroleum) to afford the title compound as a pale yellow solid (2.2 g, 7.53 mmol, 72% yield). MS (ESI) m/z 293.2 [M+H]+.

Workup

customAfter removal of the organic solvent under reduced pressure
additionthe residue was treated with water
extractionextracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customto give a crude product, which
customwas purified by silica gel column chromatography (15% ethyl acetate in petroleum)

Sources & evidence

ORD record: ord-adb2a596ef494b21838436cdcfe23310
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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