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Sodium Iodide → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-(imidazo[1,2-a]pyrimidin-2-ylmethyl)dihydro-2H-pyran-2,4(3H)-dione

HRID 1453217
Notes
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Reaction equation

HRID 1453217 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][C:18]2([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[CH2:19]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Cl[CH2:32][C:33]1[N:34]=[C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]2[CH:41]=1.[I-].[Na+]>CC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][C:18]2([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[O:23][C:22](=[O:24])[CH:21]([CH2:32][C:33]3[N:34]=[C:35]4[N:40]=[CH:39][CH:38]=[CH:37][N:36]4[CH:41]=3)[C:20](=[O:25])[CH2:19]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14179082-(Chloromethyl)imidazo[1,2-a]pyrimidineHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 575272716-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-(imidazo[1,2-a]pyrimidin-2-ylmethyl)dihydro-2H-pyran-2,4(3H)-dione
Yield 21.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (35.4 mg, 0.256 mmol) was added to a solution of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (30 mg, 0.085 mmol), 2-(chloromethyl)imidazo[1,2-a]pyrimidine (17.2 mg, 0.103 mmol) and sodium iodide (5 crystals) in acetone (40 ml). The reaction mixture was stirred at reflux for 24 hrs, after which time the mixture was acidified to pH=3 and the product was extracted with ethyl acetate (3×25 ml). The combined organics were washed with brine (30 ml), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and purified by prep HPLC to afford the title compound as a white solid (8.8 mg). 1H NMR (CDCl3): δ 1.40-1.88 (bm, 11H), 2.24 (m, 2H), 2.48-2.59 (bm, 3H), 3.79 (s, 3H), 4.03 (d, J=14.08 Hz, 1H), 4.18 (d, J=14.08 Hz, 1H), 6.94 (d, J=1.60 Hz, 2H), 7.03 (d, J=1.60 Hz, 2H), 8.08 (s, 1H), 8.82 (bs, 1H), 8.85 (bs, 1H). Exact Mass: Calcd, 481.97; Found, 481.18.

Workup

  1. temperatureat reflux for 24 hrs
  2. extractionthe product was extracted with ethyl acetate (3×25 ml)
  3. washThe combined organics were washed with brine (30 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified by prep HPLC

Sources & evidence

ORD record
ord-094bd833ebe64da3806a9ef62e3ede20
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473790B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes