Ethanol → HCID 46945343, compound

HRID 2047205Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[C:12]([N:14](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:11]3[N:31]=[CH:32][C:33]([C:34]4[CH:35]=[N:36][C:37]5[C:42]([CH:43]=4)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[C:10]3[N:9]=2)[CH2:3][CH2:2]1.CCO.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>[Cl-].[Na+].O.O.C(Cl)Cl>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[C:12]([NH2:14])[N:11]3[N:31]=[CH:32][C:33]([C:34]4[CH:35]=[N:36][C:37]5[C:42]([CH:43]=4)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[C:10]3[N:9]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To crude 5-(morpholinomethyl)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)-ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.2 g) in a 20 mL vial was added EtOH (4 mL) and then 4M HCl/dioxane (1.5 mL, 6.0 mmol). The vial was capped and heated at 85° C. for 16 hours. On cooling, saturated NaHCO3 solution (˜0.5 mL) was added, and the reaction mixture was stirred for 30 minutes. The reaction mixture was then transferred to a separatory funnel using CH2Cl2 (20 mL) and H2O (20 mL) and saturated NaHCO3 solution (20 mL) and brine (20 mL) were added. Organics were extracted with CH2Cl2 (4×30 mL), dried (Na2SO4) and concentrated in vacuo to give crude 5-(morpholinomethyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as a brown solid (0.04 g). LCMS: 0.78 mins, m/z=361.1 (MH+).

Workup

customThe vial was capped
temperatureOn cooling
customThe reaction mixture was then transferred to a separatory funnel
additionwere added
extractionOrganics were extracted with CH2Cl2 (4×30 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f3177dc6c5dd46e19c1a8e516886fcb1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

Loading…