HCID 21905816, compound → HCID 21905776, compound

HRID 1246787Notes

Reaction equation

HRID 1246787 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[C:6]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:5]=[C:4]([CH3:26])[N:3]=1>O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:26])[N:5]=[C:6]2[C:7]=1[N:8]=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])[N:18]2[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 21905816HCID 21905816, compound

Product 1

HCID 21905776HCID 21905776, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[4-chloro-6-(4-chlorophenylamino)-2-methylpyrimidin-5-yl]-2-fluorobenzamide I-(7A-80)b (0.25 g) in dioxane (6 ml) was treated with 50% propanephosphoric acid cyclic anhydride (PPM) in ethyl acetate (0.6 ml) and heated to reflux overnight. It was determined that the product was a mixture of desired product and the hydroxy compound (displacement of the chlorine atom). The reaction was therefore concentrated under reduced pressure and heated overnight in refluxing POCl3 (6 ml). The reaction mixture was concentrated to dryness, diluted with ethyl acetate, and poured onto ice. Saturated NaHCO3 solution was added next and the mixture stirred. The organic layer was separated, washed with brine, dried (Na2SO4), filtered, and concentrated to dryness. The crude product was purified via TLC preparative plate using 5% methanol/methylene chloride as the solvent to obtain the desired compound I-(7A-80)c (88 mg, 42% from 4,6-dichloro-2-isopropyl-pyrimidin-5-ylamine) as a solid: +ESI MS (M+1) 373.2; 1H NMR (400 MHz, CDCl3) δ 7.80–6.90 (m, 8H), 2.76 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight

Sources & evidence

ORD record
ord-58c4988b2eff49e6b171cf8a36e6e2a5
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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