Water → HCID 56851168, compound

HRID 1787032Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[C:5]#[C:6][C:7]1[C:12]([NH2:13])=[C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=[CH:9][N:8]=1)[CH3:2].CC(C)([O-])C.[K+].O>CN1CCCC1=O.O1CCCC1>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[NH:13][C:12]2[C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1)[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(3,3-Diethoxyprop-1-yn-1-yl)-6-phenoxypyrimidin-5-amine (2.30 g) was dissolved in 1-methyl-2-pyrrolidone (7.5 mL), and the mixture was cooled to 0° C. A solution (7.6 mL) of potassium tert-butoxide in 1.0 M tetrahydrofuran was added dropwise to this solution, and the mixture was stirred at 0° C. for 30 min. and at room temperature for 1.5 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50) to give the title compound (1.34 g) as a pale orange solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50)

Sources & evidence

ORD record: ord-2538e21d79e144199f66b16900906621
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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