Acetic Acid → HCID 137329041, compound

HRID 1262220Notes

Reaction equation

[C:1]([SiH2:5][O:6][C:7]([CH3:26])([CH3:25])[C:8]1[CH:9]=[C:10]([C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20](SC)=[N:21]3)=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:27](O)(=O)C.OO.[O-:33][S:34]([O-:37])(=S)=O.[Na+].[Na+]>CO.C([O-])(O)=O.[Na+].O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C:1]([SiH2:5][O:6][C:7]([CH3:25])([CH3:26])[C:8]1[CH:9]=[C:10]([C:14]2[N:22]3[C:17]([CH:18]=[N:19][C:20]([S:34]([CH3:27])(=[O:37])=[O:33])=[N:21]3)=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

7-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.12 g, 2.90 mmol) was dissolved in methanol (20 mL) and sodium tungstate dihydrate (77.3 mg, 0.234 mmol), acetic acid (1.37 mL, 24.2 mmol) and 50% hydrogen peroxide (610 uL, 10.7 mmol) were added. The reaction mixture was then stirred and heated at 65° C. for 4 hours. Once the reaction was complete, 25 mL of 10% Na2S2O3 was added and the reaction was stirred for 5 minutes. The reaction was diluted with saturated NaHCO3 and the product was collected by filtration to obtain 7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (818 mg, 67%). m.p.=61-65° C.; LCMS (m/e)=418 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.40 (s, 1H), 8.21-8.06 (m, 2H), 7.77 (d, 1H, J=4.6 Hz), 7.60-7.50 (m, 1H), 7.48-7.37 (m, 2H), 4.81 (s, 2H), 3.46 (s, 3H), 0.91 (s, 9H), 0.11 (s, 6H).

Workup

stirringthe reaction was stirred for 5 minutes
filtrationthe product was collected by filtration

Sources & evidence

ORD record: ord-6c2c1e1496e7419fbe5341ea00434fbc
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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