Diisopropylethylamine → HCID 58928513, compound

HRID 852020Notes

Reaction equation

HRID 852020 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-46b745753fc74d338366bc8f1c972864
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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