Diisopropylethylamine → HCID 86634073, compound

HRID 1688065Notes

Reaction equation

HRID 1688065 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-e3f2d021bc63469cae34e7789c1924af
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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