Iodine → 6-Phenyl-2-pyridin-2-ylmethyl-isothiazolo[5,4-d]pyrimidin-3-one

HRID 367240Notes

Reaction equation

HRID 367240 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([C:11]1[C:12]([SH:23])=[N:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:15][CH:16]=1)=[O:10].II>>[C:17]1([C:14]2[N:13]=[C:12]3[S:23][N:8]([CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:9](=[O:10])[C:11]3=[CH:16][N:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 807IodineHCID 1784182364-Mercapto-2-phenyl-pyrimidine-5-carboxylic acid (pyridin-2-ylmethyl)-amide

Product 1

HCID 232879016-Phenyl-2-pyridin-2-ylmethyl-isothiazolo[5,4-d]pyrimidin-3-oneYield 81.6%

Procedure

Using the procedure of Example 20, 2.0 g (6.20 mmol) of 4-mercapto-2-phenyl-pyrimidine-5-carboxylic acid (pyridin-2-ylmethyl)-amide were treated with 1.73 g (6.82 mmol) of iodine to give 1.62 g of the title compound after recrystallization from isopropanol, mp 154-156° C.

Sources & evidence

ORD record
ord-266da56f71e2464aa20b020f5ddaaf0a
Source dataset
uspto-grants-2000_10
Patent number
US06133270

Reaction notes

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