Hydrochloric Acid → 2-Chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one

HRID 910197Notes

Reaction equation

HRID 910197 reaction equation
Cl.C(O[C:5]([C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][S:9][C:8]=1[NH2:18])=[O:6])C.[Cl:19][CH2:20][C:21]#[N:22].C(=O)([O-])O.[Na+]>O1CCOCC1.O>[Cl:19][CH2:20][C:21]1[NH:22][C:5](=[O:6])[C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][S:9][C:8]=2[N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 23741772-Chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-oneYield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride gas was bubbled through a stirred solution of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (4.94 g, 0.02 mol) and chloroacetonitrile (1.4 ml, 0.022 mol) in anhydrous 1,4-dioxane (60 ml) for about 4 hours. A thick suspension formed initially which slowly dissolved. The mixture was stirred at ambient temperature for 18 hours before being poured into water (250 ml) and basified (pH 8) by the addition of sodium hydrogen carbonate. The supernatant was then decanted to leave a gummy solid which was triturated with aqueous ethanol to give 2-chloromethyl-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one as a yellow solid (3.70 g), which was used without further purification.

Workup

  1. customA thick suspension formed initially which
  2. dissolutionslowly dissolved
  3. customThe supernatant was then decanted
  4. customto leave a gummy solid which
  5. customwas triturated with aqueous ethanol

Sources & evidence

ORD record
ord-11a41cd258654b6fa56b95d665d6651d
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

Loading…