Diisopropylethylamine → HCID 86634073, compound

HRID 1041723Notes

Reaction equation

HRID 1041723 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:13]CN(C(C)C)C(C)C.[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([Cl:30])=[CH:25][N:24]=1>CS(C)=O.C(Cl)Cl>[Cl:22][C:23]1[N:28]=[C:27]([NH:1][C:2]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=2[C:4]([NH:6][CH3:13])=[O:5])[C:26]([Cl:30])=[CH:25][N:24]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 122648222-Amino-3,5-dimethylbenzamide

Product 1

HCID 86634073HCID 86634073, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-3,5-dimethyl-benzamide (573 mg), DIEA (580 mL), and 2,4,5-trichloropyrimidine (660 mg) in DMSO was heated at 65° C. for 4.5 h, then diluted with DCM, washed with brine twice, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography to provide 460 mg of 2-(2,5-dichloropyrimidin-4-ylamino)-3,5,N-trimethyl-benzamide: 1H NMR (300 MHz, CDCl3) δ 9.3 (bs, 1H), 8.2 (s, 1H), 7.3 (s, 1H), 7.2 (s, 1H), 6.2 (bs, 1H), 3.0 (d, 3H), 2.4 (s, 3H), 2.3 (s, 3H).

Workup

  1. washwashed with brine twice
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f1799136b0b143188195167651e089ce
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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