Sodium Methoxide → 2-Methoxy-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene

HRID 1051430Notes

Reaction equation

Br[C:2]1[S:13][C:12]2[N:11]=[C:10]([CH3:14])[C:9]3[N:5]([C:6]([CH2:16][CH2:17][CH3:18])=[N:7][C:8]=3[CH3:15])[C:4]=2[N:3]=1.[CH3:19][O-:20].[Na+]>CO>[CH3:19][O:20][C:2]1[S:13][C:12]2[N:11]=[C:10]([CH3:14])[C:9]3[N:5]([C:6]([CH2:16][CH2:17][CH3:18])=[N:7][C:8]=3[CH3:15])[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Bromo-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene was dissolved in 5 mL of methanol and sodium methoxide (4.98 mg, 0.092 mmol) was added. The resulting mixture was stirred at 60° C. for 1 h. LC-MS showed complete consumption of 2-bromo-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene. After removal of the solvent under reduced pressure, 5 mL of water and 10 mL of EA were added. The organic layer was concentrated, crude product was purified by prep-HPLC to give 4 mg of the title compound.

Workup

customconsumption of 2-bromo-5,6-dimethyl-8-propyl-3-thia-1,4,7,8a-tetraaza-as-indacene
customAfter removal of the solvent under reduced pressure, 5 mL of water and 10 mL of EA
additionwere added
concentrationThe organic layer was concentrated
customcrude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-4f4d8dcc008a4fd79e479f0a0dab0242
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388180B2

Reaction notes

Loading…