Sodium Iodide → HCID 21196316, compound

HRID 1066977Notes

Reaction equation

HRID 1066977 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:11]([C:21]([O:23][CH3:24])=[O:22])=[C:10]([CH3:25])[N:9]=[C:8]1[CH2:26][O:27][CH3:28].Cl.[CH3:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[F:20][C:15]1[CH:14]=[C:13]([CH:12]2[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:40]3[CH2:41][CH2:42][C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[CH3:30])([C:43]4[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=4)[CH2:38][CH2:39]3)[C:8]([CH2:26][O:27][CH3:28])=[N:9][C:10]([CH3:25])=[C:11]2[C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][C:16]=1[F:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10742569HCID 10742569, compoundHCID 21196347HCID 21196347, compound

Product 1

HCID 21196316HCID 21196316, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (+)-1-(5-bromopentyl)-6-(3,4-difluorophenyl)-1,6-dihydro-5-methoxycarbonyl-2-methoxymethyl-4-methylpyrimidine (0.08 g, 0.17 mmol.), 4-(2-methylphenyl)-4-(4-methylphenyl)piperidine hydrochloride (0.063 g, 0.21 mmol.), potassium carbonate (0.14 g, 1.0 mmol.), sodium iodide (26 mg, 0.17 mmol.) and acetone (6 mL) was refluxed overnight. The undissolved solid was then filtered off and the solvent was evaporated. The residue was flash chromatographed over silica gel (eluent: 10:1 ethyl acetate/2M ammonia in methanol) to give the title compound in 89% yield (0.1 g) as a yellow oil. Treatment of the free base with 2 equivalents of 1M HCl in ether gave the HCl salt as a pale yellow solid: mp 137-140° C.; [α]D=56.5 (1.65 mg/mL, MeOH). Anal. Calc. for C39H47F2N3O3.2HCl.2H2O.0.75CHCl3: C, 56.68; H, 6.43; N, 4.99. Found: C, 56.55; H, 6.19; N, 5.02.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe undissolved solid was then filtered off
  3. customthe solvent was evaporated
  4. customchromatographed over silica gel (eluent: 10:1 ethyl acetate/2M ammonia in methanol)

Sources & evidence

ORD record
ord-fcb3537373ee4b6cae5802d4bc440493
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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