n'-[4-Cyano3-(4-nitrobenzyl)-5-isothiazolyl]imidoformamide → 3-(4-Nitrobenzyl)isothiazolo[5,4-d]pyrimidin-4-amine

HRID 227633Notes

Reaction equation

HRID 227633 reaction equation
[C:1]([C:3]1[C:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:5][S:6][C:7]=1[N:8]=[CH:9][NH2:10])#[N:2].O(C)[Li]>CO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:4]2[C:3]3[C:7](=[N:8][CH:9]=[N:10][C:1]=3[NH2:2])[S:6][N:5]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 69060546n'-[4-Cyano3-(4-nitrobenzyl)-5-isothiazolyl]imidoformamideHCID 178419045HCID 178419045, compound

Product 1

HCID 577562803-(4-Nitrobenzyl)isothiazolo[5,4-d]pyrimidin-4-amineYield 47.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of Example 338B (0.37 g, 1.29 mmol) in methanol (3 mL) was treated with LiOCH3 (1.4 mL, 1M in methanol), and heated to 70° C. for 4 hours. The reaction was cooled to room temperature resulting in a brown precipitate which was collected by filtration. The filter cake was washed with cold methanol and dried to provide 0.175 g of the desired product. MS (ESI(+)) m/e 288 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customresulting in a brown precipitate which
  3. filtrationwas collected by filtration
  4. washThe filter cake was washed with cold methanol
  5. customdried

Sources & evidence

ORD record
ord-c271bf7ee8094ec083262377f4e99461
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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