Sodium Chloride → HCID 71239587, compound

HRID 1403226Notes

Reaction equation

HRID 1403226 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[H-].[Na+].Cl[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34].[Na+].[Cl-]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 70979645HCID 70979645, compound

Product 1

HCID 71239587HCID 71239587, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(2-aminopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxylate (1.0 g, 2.8 mmol) in dry THF (40 mL) cooled to 0° C. NaH 60% (1.342 g, 3.36 mmol) was added portion wise and the reaction mixture stirred for 30 min. (2-Chloromethoxy-ethyl)-trimethyl-silane (0.417 mL, 3.36 mmol) was added drop wise. The reaction mixture was allowed to warm up slowly to room temperature and stirred for 2 h. Saturated aqueous NaCl (30 mL) was added at 0° C. and the mixture was extracted with EtOAc (2×35 mL). The separated organic phase was dried over sodium sulfate and the solvent evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 98/2) to afford the title compound as an orange oil (0.80 g, 57%).

Workup

  1. additionwas added drop wise
  2. extractionthe mixture was extracted with EtOAc (2×35 mL)
  3. dry with materialThe separated organic phase was dried over sodium sulfate
  4. customthe solvent evaporated
  5. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-3c26b3d52a15488aaa7e67bedce9f7d9
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…