Water → 4-Amino-6-[(S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamino]pyrimidine-5-carbonitrile

HRID 243188Notes

Reaction equation

HRID 243188 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Br:11][C:12]1[C:17]2[N:18]([CH3:24])[C:19]([C@@H:21]([NH2:23])[CH3:22])=[N:20][C:16]=2[CH:15]=[CH:14][C:13]=1[F:25].CCN(C(C)C)C(C)C.O>CC(O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:23][C@H:21]([C:19]2[N:18]([CH3:24])[C:17]3[C:12]([Br:11])=[C:13]([F:25])[CH:14]=[CH:15][C:16]=3[N:20]=2)[CH3:22])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 68157037(S)-1-(7-Bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamine

Product 1

HCID 681575724-Amino-6-[(S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamino]pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Amino-6-chloropyrimidine-5-carbonitrile (0.88 g, 5.71 mmol) was added to a solution of (S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamine (1.11 g, 4.08 mmol) and DIPEA (2.6 mL, 14.7 mmol) in IPA (30 mL) and the resultant mixture stirred at 85° C. for 16 h. The reaction mixture was poured into water and the precipitated solid removed by filtration. The solid was washed with water and dried to give the title compound as an off white solid (1.61 g, 100%). LCMS (Method C): RT 2.68 min [M+H]+ 390.1, 392.1

Workup

  1. customthe precipitated solid removed by filtration
  2. washThe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-be3dbf5cedac4c1480bdb53468a3324c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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