Sodium hydride → HCID 24856780, compound

HRID 853763Notes

Reaction equation

HRID 853763 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:5]=1[O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:13]2[CH2:16][CH3:17])=[CH:9][N:8]=1.Br[CH2:32][C:33]([NH:35][CH3:36])=[O:34]>C1COCC1.O>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N:18]([C:12]1[N:13]([CH2:16][CH3:17])[C:14]2[C:10]([N:11]=1)=[CH:9][N:8]=[C:7]([O:6][C:5]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:4]=1[F:3])[N:15]=2)[CH2:32][C:33]([NH:35][CH3:36])=[O:34]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 154907452-Bromo-N-methylacetamideHCID 24857371HCID 24857371, compound

Product 1

HCID 24856780HCID 24856780, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 0.010 g, 0.25 mmol) is added to a solution of [2-(2,6-difluorophenoxy)-9-ethyl-9H-purin-8-yl]-(2-chlorophenyl)-amine, 14, (0.1 g, 0.25 mmol) in THF (3 mL). After 5 minutes at room temperature 2-bromo-N-methyl-acetamide (0.06 mL, 0.37 mmol) is added and stirring is continued for 1 hour. The mixture is diluted with H2O (25 mL) and extracted three times with EtOAc (50 mL). The combined organic layers are washed with brine, dried over MgSO4, concentrated in vacuo and the residue purified by HPLC to afford 45 mg (38% yield) of the desired product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.54 (s, 1H), 7.54-7.59 (m, 2H), 7.15-7.36 (m, 4H), 7.04 (t, J=7.8 Hz, 2H), 4.53 (s, 2H), 3.61 (q, J=7.2 Hz, 2H), 2.85 (d, J=4.8 Hz, 3H), 0.99 (t, J=7.2 Hz, 3H); ESI/MS: 473 (M+H).

Workup

  1. extractionextracted three times with EtOAc (50 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-f45bafcb7af646fe9c1ac475cd70a6a0
Source dataset
uspto-grants-2007_08
Patent number
US07256196B1

Reaction notes

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