Ethanol → HCID 69199848, compound

HRID 750808Notes

Reaction equation

HRID 750808 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[C:9](S(C)(=O)=O)[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:4])=[O:3].C(O)C.CN.FC1C=C(C=CC=1F)CO[C:41]1N=C(NC)C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2Cl)[N:42]=1>C(#N)C>[CH3:1][S:2]([C:5]1[N:10]=[C:9]([CH2:41][NH2:42])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[N:6]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 10391494HCID 10391494, compoundHCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Product 1

HCID 69199848HCID 69199848, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask fitted with a magnetic stirrer bar and rubber septum was added 2,4-bis(methylsulfonyl)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]-pyrimidine (Reference Example 5, Step A, 50 mg, 0.1 mmol), and 1 mL each of ethanol and acetonitrile. The mixture was cooled to 0° and methylamine (2 eq., 400 μL, 1M in THF) was added via syringe. The mixture was stirred for 1 h, the solvents removed under reduced pressure and the product chromatographed (77/23 hexanes/ethyl acetate) to give two products: a higher Rf product (unidentified) and 2-(3,4-difluorobenzyloxy)-4-(N-methylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine as the lower Rf product. HPLC/MS: m/e=442 (M+−1); Rt=3.58 min. 1H-NMR 500 MHz (CDCl3): δ 3.13 (d, J=5 Hz, 3H), 3.37 (s, 3H), 7.07 (d, J=8 Hz 1H), 7.10 (d, J=8 Hz, 2H), 7.18 (d, J=8 Hz, 1H), 7.38-7.40 (m, 3H).

Workup

  1. customTo a round bottom flask fitted with a magnetic stirrer bar
  2. temperatureThe mixture was cooled to 0°
  3. customthe solvents removed under reduced pressure
  4. customthe product chromatographed (77/23 hexanes/ethyl acetate)
  5. customto give two products

Sources & evidence

ORD record
ord-cd8587e5a94243a0ae8f65c622ff6218
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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