Sodium Iodide → 5-[1-(2-Bromo-phenylamino)-ethyl]-2-methylsulfanyl-pyrimidin-4-yl-methyl-amine

HRID 1247653Notes

Reaction equation

HRID 1247653 reaction equation
Cl[CH:2]([C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1)[CH3:3].[I-].[Na+].[Br:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].C(N(C(C)C)C(C)C)C>C(#N)C.O>[Br:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][CH:2]([C:4]1[C:5]([NH:12][CH3:13])=[N:6][C:7]([S:10][CH3:11])=[N:8][CH:9]=1)[CH3:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 119922-BromoanilineHCID 81531DiisopropylethylamineHCID 21908981[5-(1-Chloro-ethyl)-2-methylsulfanyl-pyrimidin-4-yl]-methyl-amine

Product 1

HCID 219089795-[1-(2-Bromo-phenylamino)-ethyl]-2-methylsulfanyl-pyrimidin-4-yl-methyl-amineYield 38.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

0.25 g of the product from Example 11b, supra, and 34 mg sodium iodide in 10 mL acetonitrile were stirred for 15 min at RT. The resulting suspension was added drop-wise at RT to a mixture of 0.21 g 2-bromoaniline (Aldrich) and 0.33 g N-ethyl-di-isopropyl amine (Aldrich) in 5 mL acetonitrile. Stirring was continued for 16 hrs and the mixture was diluted with 20 mL water and extracted with dichloromethane. Chromatography on silica (eluent CHCl3) yielded 158 mg of the title product.

Workup

  1. additionThe resulting suspension was added drop-wise at RT
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-b4f91d0912544e099b5ce3690a144676
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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