Benzoyl chloride → HCID 67252215, compound

HRID 2421006Notes

Reaction equation

HRID 2421006 reaction equation
C1COCC1.Cl[C:7]1[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19].C(Cl)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:17]([NH:20][C:7]1[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=1)[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 7852PropylamineHCID 8028TetrahydrofuranHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile2×

Product 1

HCID 67252215HCID 67252215, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 40 mL of THF, 4-chloro-5-cyano-2-methylthiopyrimidine [Compound (V)] (1.86 g, 10.0 mmol) obtained in Reference Example 4 was dissolved, then n-propylamine (709 mg, 12.0 mmol) and morpholinomethylpolystyrene (7.0 g) were added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction was confirmed by thin-layer chromatography, chloroform (100 mL) and benzoylchloride polymer bound [about 2.5 mmol/g, 4.6 g, Canadian Journal of Chemistry, Vol. 55, p. 3351 (1977)] were added thereto, followed by further stirring at room temperature for 12 hours. After resins in the reaction mixture were filtered out, the filtrate was concentrated under reduced pressure to give 4-n-propylamino-5-cyano-2-methylthiopyrimidine [Compound (W) in which R1 represents n-propylamino].

Workup

  1. dissolutionwas dissolved
  2. additionwere added
  3. stirringby further stirring at room temperature for 12 hours
  4. filtrationAfter resins in the reaction mixture were filtered out
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49ec7bf9c8d94c889f2ffa7f47a4d52a
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

Loading…