Potassium Carbonate → HCID 67983634, compound

HRID 1397173Notes

Reaction equation

HRID 1397173 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([CH3:18])=[N:9][C:10]([N:13]=CN(C)C)=[N:11][CH:12]=1)=O.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH2:31])=[NH:30])=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29]2[N:31]=[C:5]([C:7]3[C:8]([CH3:18])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=3)[CH:4]=[CH:3][N:30]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68032343HCID 68032343, compoundHCID 178479387HCID 178479387, compound

Product 1

HCID 67983634HCID 67983634, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N′-{5-[(2E)-3-(dimethylamino)prop-2-enoyl]-4-methylpyrimidin-2-yl}-N,N-dimethylimidoformamide (27) (50 mg, 0.191 mmol), 1-(4-fluorophenyl)guanidine hydrochloride (102 mg, 0.383 mmol), and K2CO3 (106 mg, 0.765 mmol) in DMF (1018 μl) was heated at 120° C. for 2 d. The crude product was filtered through a syringe filter, then the crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] to obtain ˜80% pure desired product. The product was taken up in 10% MeOH/DCM, then was purified by Biotage™ silica gel chromatography [10 g SNAP column, 2-10% MeOH/DCM] and further purified by trituration with acetone and acetonitrile to obtain the desired product as a pale yellow solid (10.23 mg, 18% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.47 (s, 3 H) 6.93 (s, 2 H) 7.02 (d, J=5.05 Hz, 1 H) 7.12 (t, J=8.84 Hz, 2 H) 7.77 (dd, J=9.35, 4.80 Hz, 2 H) 8.44 (s, 1 H) 8.46 (d, J=5.05 Hz, 1 H) 9.61 (s, 1 H). HRMS (ES+) for C15H13FN6.H+ [MH+]: calcd, 297.1264. found, 297.1274. UV-LC: 98.95/100% UV purity at 214/254 nm; tR=4.30 minutes over 7.75 minutes.

Workup

  1. filtrationThe crude product was filtered through a syringe
  2. filtrationfilter
  3. customthe crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes]

Sources & evidence

ORD record
ord-a83cd4c648a94cadad42d367d1f7bf29
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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