Bromoacetonitrile → HCID 131724089, compound

HRID 987546Notes

Reaction equation

HRID 987546 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([N:9]([O:25][SiH:26]([CH3:28])[CH3:27])[C:10]2[CH:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[Br:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:34][C:35]#[N:36]>>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([N:9]([O:25][SiH:26]([CH3:27])[CH3:28])[C:10]2[CH:15]=[C:14]([N:16]([CH2:34][C:35]#[N:36])[C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[Br:24])[N:13]=[CH:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 131724090HCID 131724090, compound

Product 1

HCID 131724089HCID 131724089, compoundYield 37%

Procedure

To a solution of 4-(4-tertbutyldimethylsilyloxyanilino)-6-(2-bromo-4-methylanilino)pyrimidine (Reference Example 3, 396 mg) in tetrahydrofuiran (1 ml) under nitrogen atmosphere was added portion wise sodium hydride (60% dispersion in mineral oil, 58 mg). The solution was stirred for 30 minutes. Bromoacetonitrile (131 mg) was added and the reaction stirred for a further 1 hour. The solvent was evaporated and the residue purified by column chromatography eluting with DCM:MeOH:concentrated ammonia; 97.8:2:0.2 to give the title compound (158 mg, 37%) as a solid. M/z 524 (MH+).

Workup

  1. stirringthe reaction stirred for a further 1 hour
  2. customThe solvent was evaporated
  3. customthe residue purified by column chromatography
  4. washeluting with DCM

Sources & evidence

ORD record
ord-ee7534ec3a0947e1b1e2f565c7dc574b
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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