Triethylamine → HCID 68195278, compound

Participants

Reaction Conditions

Reaction Steps

2-(1-(tert-Butyldimethylsilyl)-1H-indol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x12, 42 mg, 0.100 mmol) in CH2Cl2 (1 mL) was cooled to 0° C. 2-(4-Methoxyphenyl)acetyl chloride (0.018 mL, 0.120 mmol) was added, followed by triethylamine (0.028 mL, 0.199 mmol) to give a yellow solution. The reaction mixture was stirred for 2 hours at 0° C. The solvent was subsequently removed in vacuo and the resulting concentrate was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetatehexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow oil (42 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ 0.64 (s, 6 H), 0.89 (s, 9 H), 3.02-3.22 (m, 4 H), 3.42-3.61 (m, 2 H), 3.66-3.78 (m, 3 H), 3.87-3.92 (m, 2 H), 3.91-3.98 (m, 1 H), 4.30-4.47 (m, 1 H), 4.64-4.75 (m, 1 H), 6.79-6.93 (m, 2 H), 7.00-7.30 (m, 3 H), 7.42-7.51 (m, 2 H), 7.61-7.68 (m, 1 H), 8.02-8.07 (m, 1 H), 8.32-9.02 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C32H39N5O3Si, 570.28; found 570.6.

Provenance & Evidence