Triethylamine → HCID 86756054, compound

HRID 1858239Notes

Reaction equation

HRID 1858239 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C>O1CCOCC1>[CH2:25]([O:24][C:22]([CH2:21][C:17]1[CH:16]=[C:15]([NH:14][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)[CH:20]=[CH:19][CH:18]=1)=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13042040Ethyl 2-(3-aminophenyl)acetateHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86756054HCID 86756054, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5 g (21.5 mmol) of ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate and 4 g (22.3 mmol) of ethyl 3-aminophenylacetate in 80 ml of 1,4-dioxan was treated with 6 ml (43 mmol) of triethylamine and then heated at 60° C. for 4 hours. The mixture was cooled and evaporated. The residue was partitioned between 120 ml of ethyl acetate and 100 ml of 2M hydrochloric acid. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 7.4 g (92%) of ethyl 4-[3-(ethoxycarbonylmethyl)phenyl]amino-2-methylthiopyrimidine-5-carboxylate as a pale orange colored oil which solidifies slowly to a white solid. [Mass spectrum (ESI) MH+ =376].

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated
  3. customThe residue was partitioned between 120 ml of ethyl acetate and 100 ml of 2M hydrochloric acid
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-76ca81a53c5f40359fad061ad22cb3b0
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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