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Sodium Carbonate → 2-(4-{2-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazin-1-yl)acetamide

HRID 1455762
Notes
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Reaction equation

HRID 1455762 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH2:17])=[O:16])[CH2:10][CH2:9]2)[C:5]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:4]([CH3:30])[N:3]=1.[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH2:17])=[O:16])[CH2:10][CH2:9]2)[C:5]([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[CH3:29])=[C:4]([CH3:30])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 575315092-{4-[2-Chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide

Product 1

HCID 575313962-(4-{2-(2,6-Dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-6-methylpyrimidin-4-yl}piperazin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-{4-[2-chloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidin-4-yl]-piperazin-1-yl}-acetamide (20 mg, 0.05 mmol), 2,6-dimethylphenylboronic acid (21 mg, 0.14 mmol) and 2 M sodium carbonate (0.14 mL, 0.28 mmol) in dioxane (1 mL) is degassed with bubbling argon for 20 min. Pd(PPh3)4 (2.9 mg, 5 mol %) is added and the reaction mixture is heated at 100° C. under nitrogen with magnetic stirring. After 18 h, the reaction mixture is partitioned between EtOAc (10 mL) and water (2 mL), the organic layer is separated, washed with brine (2 mL), dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain a dark oil. Purification on silica gel (3% MeOH/CH2Cl2 0.1% NH4OH) provides the title compound as a colorless film. LC/MS (Method 3), M+H=502.3, Rt=2.43 min.; 1H NMR (CDCl3) δ=7.07-7.19 (m, 4H), 6.82 (m, 2H), 5.44 (br, s, 1H), 4.97 (s, 2H), 3.57 (br, s, 4H), 3.02 (s, 2H), 2.91 (m, 1H), 2.62 (m, 4H) 2.56 (s, 3H), 2.22 (s, 3H), 2.16 (s, 6H), 1.28 (d, 6H).

Workup

  1. customis degassed with bubbling argon for 20 min
  2. additionPd(PPh3)4 (2.9 mg, 5 mol %) is added
  3. customthe reaction mixture is partitioned between EtOAc (10 mL) and water (2 mL)
  4. customthe organic layer is separated
  5. washwashed with brine (2 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated at reduced pressure
  9. customto obtain a dark oil
  10. customPurification on silica gel (3% MeOH/CH2Cl2 0.1% NH4OH)

Sources & evidence

ORD record
ord-0cb367f6dcc848f9b55d1505e4082928
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07482350B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes