Acetic Acid → 7-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

HRID 1262301Notes

Reaction equation

[OH-].[Na+].CS([C:6]1[N:11]=[CH:10][C:9]2=[CH:12][CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[N:8]2[N:7]=1)=O.C(O)(=[O:25])C>O>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]1[N:8]2[C:9]([CH:10]=[N:11][C:6]([OH:25])=[N:7]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 8-dram vial, 19.10 M of Sodium hydroxide in Water (10.0 mL, 191 mmol) and Water (10.0 mL) water were added. The mixture was heated at 100° C. 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (2.00 g, 6.96 mmol) was added portion wise over 10 minutes. The reaction mixture was heated at 120° C. for 60 minutes. HPLC suggested no SM. The reaction was cooled to room temperature. Glacial acetic acid was added to adjust pH to 4. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and subsequently with Et2O. The resulting solid was dried under vacuum overnight to give 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol as a yellow solid (1.50 g, 85%). LCMS 242.15 (M+H).

Workup

temperatureThe reaction mixture was heated at 120° C. for 60 minutes
temperatureThe reaction was cooled to room temperature
filtrationThe solid was filtered
washwashed with water and subsequently with Et2O
customThe resulting solid was dried under vacuum overnight

Sources & evidence

ORD record: ord-eef7d36cfb764497a912e816dc41c739
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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