Triethylamine → HCID 12904738, compound

HRID 1679903Notes

Reaction equation

HRID 1679903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:19]([NH2:20])=[N:18][C:12]2[N:13]=[C:14]([CH3:17])[N:15]=[CH:16][C:11]=2[CH:10]=1.[C:21](N1C=CN=C1)([N:23]1[CH:27]=CN=[CH:24]1)=[O:22].Cl.CNC.C(N(CC)CC)C>ClCCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:19]([NH:20][C:21]([N:23]([CH3:27])[CH3:24])=[O:22])=[N:18][C:12]2[N:13]=[C:14]([CH3:17])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 12904727HCID 12904727, compound

Product 1

HCID 12904738HCID 12904738, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following the procedure of Example 11, 3.0 g of 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine and 2.0 g of carbonyldiimidazole are reacted at reflux in 50 ml of 1,2-dichloroethane for 24 hours. The mixture is cooled, treated sequentially with 1.5 g of dimethylamine hydrochloride and 2 ml of triethylamine, and stirred at room temperature for 1.5 hours. It is then washed with water prior to chromatography over 150 g of silica gel. The product is eluted with a 99/1 chloroform/methanol mixture and recrystallized from ethyl acetate to give N-[6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-yl]-N',N'-dimethylurea, mp 177°-181° C.

Workup

  1. customare reacted
  2. temperatureThe mixture is cooled
  3. washIt is then washed with water
  4. washThe product is eluted with a 99/1 chloroform/methanol mixture
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-96ef8367eb8b4793a3546890a77959c2
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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