Diisopropylethylamine → HCID 58928513, compound

HRID 1666063Notes

Reaction equation

HRID 1666063 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([NH:19][CH3:20])=[O:18].CCN(C(C)C)C(C)C>C1COCC1>[Cl:10][C:6]1[N:5]=[C:4]([S:11][CH3:12])[N:3]=[C:2]([NH:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([NH:19][CH3:20])=[O:18])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 126079733-Amino-N,4-dimethylbenzamide

Product 1

HCID 58928513HCID 58928513, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (2.19 g, 10 mmol), 3-amino-4,N-dimethyl-benzamide (1.64 g, 10 mmol), and DIEA (1.40 g, 18.8 mmol) were mixed in THF (20 mL). The resulting mixture was stirred at room temperature for overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was concentrated and the crude product was purified by flash chromatography to obtain 3-(6-chloro-5-cyano-2-methylsulfanyl-pyrimidin-4-ylamino)-4,N-dimethyl-benzamide (2.78 g, 80%). MS (m/z): 348 (M+H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated
  4. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a698c5dbb9964528a16215a50cdb8b78
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

Loading…