Potassium Carbonate → 2-{4-[2-Chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide

HRID 1455761Notes

Reaction equation

HRID 1455761 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH2:16][O:17][C:18]2[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[CH:21]=[CH:20][C:19]=2[CH3:27])=[C:11]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[N:10]=1.Br[CH2:35][C:36]([NH2:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Cl:8][C:9]1[N:10]=[C:11]([N:28]2[CH2:29][CH2:30][N:31]([CH2:35][C:36]([NH2:38])=[O:37])[CH2:32][CH2:33]2)[C:12]([CH2:16][O:17][C:18]2[CH:23]=[C:22]([CH:24]([CH3:25])[CH3:26])[CH:21]=[CH:20][C:19]=2[CH3:27])=[C:13]([CH3:15])[N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 866021422-chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-4-methyl-6-piperazin-1-yl-pyrimidine Trifluoroacetic Acid Salt

Product 1

HCID 575315092-{4-[2-Chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-4-methyl-6-piperazin-1-yl-pyrimidine trifluoroacetic acid salt (722 mg), 2-bromoacetamide (290 mg, 2.11 mmol) and potassium carbonate (871 mg, 6.30 mmol) in DMA (10 mL) is stirred at room temperature for 3 h. The reaction mixture is partitioned between EtOAc (30 mL) and water (10 mL), the organic layer is separated, washed with water (10 mL×2), brine (10 mL), dried over sodium sulfate, filtered and evaporated at reduced pressure to yield a yellow oil. Purification by chromatography on silica gel affords the title compound as a colorless oil that solidifies on standing. 1H NMR (CDCl3) δ=7.10 (d, 1H), 6.92 (br, s, 1H), 6.82 (d, 1H), 6.74 (s, 1H), 5.54 (br, s, 1H), 4.83 (s, 2H), 3.61, (m, 4H), 3.04 (s, 2H) 2.90 (m, 1H), 2.63 (m, 4H), 2.47 (s, 3H), 2.14 (s, 3H), 1.27 (d, 6H).

Workup

  1. customThe reaction mixture is partitioned between EtOAc (30 mL) and water (10 mL)
  2. customthe organic layer is separated
  3. washwashed with water (10 mL×2), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated at reduced pressure
  7. customto yield a yellow oil
  8. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-5da1f7bff85a42d191baa9f5f7390377
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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