Water → HCID 69872991, compound

HRID 1699360Notes

Reaction equation

HRID 1699360 reaction equation
[C:1]([C:3]1[CH2:8][N:7]2[CH:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10](=[O:12])[CH:11]=[C:6]2[N:5]([CH3:18])[C:4]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)#[N:2].[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]Br.O>CN(C=O)C.[Ag-]=O>[C:1]([C:3]1[CH:4]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:5]([CH3:18])[C:6]2[N:7]([CH:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10](=[O:12])[CH:11]=2)[C:8]=1[CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[F:27])#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 67968alpha-Bromo-o-fluorotolueneHCID 18319887HCID 18319887, compound

Product 1

HCID 69872991HCID 69872991, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To 3-cyano-6-ethoxycarbonyl-2-(4-methoxyphenyl)- 1-methyl-4H -pyrrolo[1,2-a]pyrimid-7-one (351 mg, 1.0 mmol.) in dry DMF (5 mL) under N2, 2-fluorobenzyl bromide (473 mg, 2.5 mmol) and silver(I) oxide (924 mg, 4 mmol) were added. The slurry was stirred for 2 days at room temperature and poured into water (10 mL). Crude product was extracted out from water by ethyl acetate (50 mL). The organic layer was then concentrated and purified by silica gel chromatography (ethyl acetate/hexane) to give a pure product. It was crystallized in ether/ethyl acetate to give the titled compound as off white crystals (310 mg, 52%); proton NMR (DMSO-d6): 8.67 (1H, s), 7.45-7.80 (6H, m), 7.00 (2H, d, J=7.8 Hz), 5.70 (2H, s), 4.18 (2H, q, J=6.6 Hz), 3.74 (3H, s), 2.56 (3H, s), 1.23 (3H, t, J=6.6 Hz); MS: 460 (MH+).

Workup

  1. extractionCrude product was extracted out from water by ethyl acetate (50 mL)
  2. concentrationThe organic layer was then concentrated
  3. custompurified by silica gel chromatography (ethyl acetate/hexane)
  4. customto give a pure product
  5. customIt was crystallized in ether/ethyl acetate

Sources & evidence

ORD record
ord-50568fb413564b6db30889cbeae300a9
Source dataset
uspto-grants-2002_02
Patent number
US06346534B1

Reaction notes

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