alpha-Bromo-o-fluorotoluene → 2-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanol

HRID 1097365Notes

Reaction equation

HRID 1097365 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([SH:24])=[N:15][C:14]=2[N:25]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.CN1CCCC1=O>[NH2:10][C:11]1[S:12][C:13]2[C:18]([NH:19][C@H:20]([CH3:23])[CH2:21][OH:22])=[N:17][C:16]([S:24][CH2:4][C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[F:1])=[N:15][C:14]=2[N:25]=1

Participants

5

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 178461804HCID 178461804, compound

Product 1

HCID 235198222-[[2-amino-5-[[(2-fluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-(2R)-1-propanolYield 35%

Reagents, catalysts & solvents 1

HCID 18784345DMSO N-methylpyrrolidinoneSolvent

Procedure

2-fluorobenzylbromide (0.369 g) was added portionwise to a solution of the product of example 32 step b) (0.5 g) and diisopropylethylamine (0.26 g) in DMSO/N-methylpyrrolidinone (4 ml/0.5 ml) at 50° C. and stirring maintained for 1 h. The mixture was partitioned between H2O (200 ml) and EtOAc (120 ml). The organics were recovered and washed further with H2O (200 ml), dried over MgSO4 and concentrated onto silica gel. The subtitle compound was purified by flash chromatography using DCM then EtOAc as eluents to yield a white solid (245 mg, 35%).

Workup

  1. temperaturemaintained for 1 h
  2. customThe mixture was partitioned between H2O (200 ml) and EtOAc (120 ml)
  3. customThe organics were recovered
  4. washwashed further with H2O (200 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated onto silica gel
  7. customThe subtitle compound was purified by flash chromatography

Sources & evidence

ORD record
ord-f468bf323fc64e37bfbd8ea6088e7cb5
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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