Tert-Butyl nitrite → HCID 178518542, compound

HRID 393182Notes

Reaction equation

HRID 393182 reaction equation
N[C:2]1[S:3][C:4]2[C:9](=[O:10])[N:8]=[C:7]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[NH:6][C:5]=2[N:26]=1.N(OC(C)(C)C)=O>O1CCCC1>[O:19]([C:15]1[CH:14]=[C:13]([CH2:12][S:11][C:7]2[NH:6][C:5]3[N:26]=[CH:2][S:3][C:4]=3[C:9](=[O:10])[N:8]=2)[CH:18]=[CH:17][CH:16]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 178508257HCID 178508257, compound

Product 1

HCID 178518542HCID 178518542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-[[(3-phenoxyphenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7(4H)-one (0.3 g) (product of Example 5) was added over 90 minutes to a solution of t-butyl nitrite (0.17 mL) in tetrahydrofuran (3 mL) at 65° C. After a further 3.5 hours at 65° C., the solvent was evaporated and the residue chromatographed on silica eluting with methanol/dichloromethane mixtures to give the title compound. Yield 0.071 g.

Workup

  1. customthe solvent was evaporated
  2. customthe residue chromatographed on silica eluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-9da0e437312047a4a976a27afc0980e4
Source dataset
uspto-grants-2004_10
Patent number
US06806273B1

Reaction notes

Loading…