Bromoform → 2-Bromo-7-chloro-5-((2,3-difluorobenzyl)thio)thiazolo[4,5-d]pyrimidine

HRID 1006507Notes

Reaction equation

HRID 1006507 reaction equation
[Cl:1][C:2]1[C:3]2[S:20][C:19](N)=[N:18][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1.N(OC(C)(C)C)=O.C(Br)(Br)[Br:30]>>[Br:30][C:19]1[S:20][C:3]2[C:2]([Cl:1])=[N:7][C:6]([S:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=3[F:17])=[N:5][C:4]=2[N:18]=1

Participants

4

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 112216507-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]-thiazolo[4,5-d]pyrimidin-2-amine

Product 1

HCID 226713342-Bromo-7-chloro-5-((2,3-difluorobenzyl)thio)thiazolo[4,5-d]pyrimidine

Conditions

Temperature
60 °C

Procedure

The product of example 4 step (b) (8.0 g) was suspended in bromoform (200 ml) followed by addition of tert-butyl nitrite (8 ml) and the whole heated at 60° C. for 30 minutes. The solvents were removed by reduced pressure and the residue purified by column chromatography (silica-1:1-dichloromethane/isohexane) to give a yellow solid (5.6 g).

Workup

  1. customThe solvents were removed by reduced pressure
  2. customthe residue purified by column chromatography (silica-1:1-dichloromethane/isohexane)

Sources & evidence

ORD record
ord-79028aa76ade4298804e523819462a1c
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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