Ethanol → (E)-4-[(4-Amino-6-chloro-2-pyrimidinyl)thio]-2-butenoic acid methyl ester

HRID 1637717Notes

Reaction equation

HRID 1637717 reaction equation
S(O)(=O)(=O)C.[NH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[N:10]=[C:9]([SH:14])[N:8]=1.C(O)C.Br[CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23]>[OH-].[Na+]>[CH3:25][O:24][C:22](=[O:23])/[CH:21]=[CH:20]/[CH2:19][S:14][C:9]1[N:8]=[C:7]([NH2:6])[CH:12]=[C:11]([Cl:13])[N:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 178505342HCID 178505342, compound

Product 1

HCID 6475109(E)-4-[(4-Amino-6-chloro-2-pyrimidinyl)thio]-2-butenoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-Amino-6-chloro-2-mercaptopyrimidine mesylate (0.30 g, 1.16 mmol) is dissolved in 3.25N sodium hydroxide (2 ml) and ethanol (1 ml) at ambient temperature followed by the addition of methyl 4-bromocrotonate (0.16 ml, 1.40 mmol). The reaction is stirred for 2 to 15 hours, quenched with excess water, extracted with methylene chloride (2×25 ml). The extracts are combined, washed with saline (25 ml), dried over sodium sulfate, concentrated in vacuo and recrystallized from hexane/ethyl acetate to give Cpd #193. mp 146-149° C.

Workup

  1. customquenched with excess water
  2. extractionextracted with methylene chloride (2×25 ml)
  3. washwashed with saline (25 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customrecrystallized from hexane/ethyl acetate
  7. customto give Cpd #193

Sources & evidence

ORD record
ord-4826e61ff721479592517ce854833e32
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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