Dimethylformamide → HCID 86633986, compound

HRID 1687604Notes

Reaction equation

HRID 1687604 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:3]=1[NH2:14].CN(C=O)C.[H-].[Na+].[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([Cl:30])=[CH:25][N:24]=1>>[Cl:22][C:23]1[N:28]=[C:27]([NH:14][C:3]2[C:4]([S:8]([CH:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:26]([Cl:30])=[CH:25][N:24]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 67264214HCID 67264214, compound

Product 1

HCID 86633986HCID 86633986, compound

Conditions

Temperature
0 °C

Procedure

2-Fluoro-6-(propane-2-sulfonyl)-phenylamine (3.10 g, 14 mmol) in DMF (10 mL, 0.1 mol) was treated with Sodium hydride, 60% disp. in mineral oil (1.14 g) at 0° C., then 2,4,5-Trichloro-pyrimidine (1.80 mL, 0.0157 mol) was added. The reaction was stirred for 30 minutes at 0° C. and then allowed to warm to rt and stirred at rt for 3 hrs. The reaction mixture was quenched with sat'd NH4Cl Product isolated as an off-white solid: 3.24 g, 62%. MP 192-193, LCMS 365.97 (M+H), HPLC purity 97%, 1H-NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 8.31 (s, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.53-7.50 (m, 2H), 3.10-3.00 (m, 1H), 1.28 (d, J=5.8 Hz, 6H).

Workup

  1. temperatureto warm to rt
  2. stirringstirred at rt for 3 hrs
  3. customThe reaction mixture was quenched with sat'd NH4Cl Product
  4. customisolated as an off-white solid

Sources & evidence

ORD record
ord-09965b5533e84bb1969f9e4d981ac6e1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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