Hydrochloric Acid → HCID 21839347, compound

HRID 1738797Notes

Reaction equation

C([Li])CCC.[CH2:6]([N:9]([CH2:13][C:14]#[CH:15])[CH2:10][CH2:11][CH3:12])[CH2:7][CH3:8].[CH2:16]([N:18]1[C:26]2[N:25]=[CH:24][N:23]([CH2:27][CH2:28][CH3:29])[C:22]=2[C:21](=[O:30])[N:20]([CH2:31][CH2:32][CH2:33][C:34](=[O:36])[CH3:35])[C:19]1=[O:37])[CH3:17].Cl>CCCCCC.O1CCCC1>[CH2:13]([N:9]([CH2:10][CH2:11][CH3:12])[CH2:6][C:7]#[C:8][C:34]([OH:36])([CH3:35])[CH2:33][CH2:32][CH2:31][N:20]1[C:21](=[O:30])[C:22]2[N:23]([CH2:27][CH2:28][CH3:29])[CH:24]=[N:25][C:26]=2[N:18]([CH2:16][CH3:17])[C:19]1=[O:37])[CH2:14][CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

5.3 ml (8.45 mmol) of a 15% strength butyllithium solution in n-hexane were slowly added dropwise to a solution of 1.36 ml (7.8 mmol) of N,N-dipropyl-2-propynylamine in 6 ml of tetrahydrofuran at -78° C., and the mixture was stirred at -78° C. for one hour. After warming to room temperature, a solution of 2.0 g (6.5 mmol) of 3-ethyl-1-(4-oxopentyl)-7-propylxanthine in 8 ml of tetrahydrofuran was added. After 7 hours at room temperature, the mixture was adjusted to pH 6-7 with 4 N hydrochloric acid and partitioned between 5% strength sodium bicarbonate solution and dichloromethane. The organic phase was dried with magnesium sulfate, concentrated under reduced pressure and purified by flash chromatography, dichloromethane/methanol=19/1.

Workup

temperatureAfter warming to room temperature
waitAfter 7 hours at room temperature
custompartitioned between 5% strength sodium bicarbonate solution and dichloromethane
dry with materialThe organic phase was dried with magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified by flash chromatography, dichloromethane/methanol=19/1

Sources & evidence

ORD record: ord-056964b442f845449b804e1dbbf7b988
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965555

Reaction notes

Loading…