Bromoform → 2-[[2-bromo-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol

HRID 1097366Notes

Reaction equation

HRID 1097366 reaction equation
N(OCCC(C)C)=O.N[C:10]1[S:11][C:12]2[C:17]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])=[N:16][C:15]([S:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:14][C:13]=2[N:32]=1.C(#N)C.C(Br)(Br)[Br:37]>>[Br:37][C:10]1[S:11][C:12]2[C:17]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])=[N:16][C:15]([S:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:14][C:13]=2[N:32]=1

Participants

5

Reactant 4

HCID 5558BromoformHCID 6342AcetonitrileHCID 8053Isoamyl NitriteHCID 235198222-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol

Product 1

HCID 235198302-[[2-bromo-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanolYield 38%

Procedure

Isoamyl nitrite (0.3 ml) was added to a suspension of the product of example 32 step c) (0.23 g) in bromoform (15 ml) and acetonitrile (15 ml) at 50° C. Stirring was maintained for 10 min before concentrating to approximately, 3 ml. The residue was purified by column chromatography using 20% EtOAc/DCM as eluent to yield the subtitle compound as a yellow solid (102 mg, 38%).

Workup

  1. customat 50° C
  2. temperaturewas maintained for 10 min
  3. concentrationbefore concentrating to approximately, 3 ml
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-549e2d6f88dc4c73a0bb91fd22490451
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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