Trifluoroacetic acid → HCID 57556931, compound

HRID 556339Notes

Reaction equation

HRID 556339 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[CH:9][N:8]=[C:7]([S:20][CH3:21])[N:6]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl.O>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[O:2][C:3](=[O:4])[C:5]2[N:6]=[C:7]([S:20][CH3:21])[N:8]=[CH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 575569325-(2-Chlorophenylethynyl)-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 57556931HCID 57556931, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(2-chloro-phenylethynyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (5.0 g, 9.4 mmol) (prepared in a manner similar to that described above), 50% (v/v) trifluoroacetic acid in dichloromethane (15 ml) and water (1 ml) was stirred in a heavy-walled Smith process vial and irradiated to 120° C. for 45 min. The mixture was evaporated in vacuo to dryness and the residual oil was purified by flash column chromatography over silica using a 3:7 mixture of hexane and dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 6-(2-chlorophenyl)-2-methylsulfanylpyrano[3,4-d]pyrimidin-8-one (3.15 g) as a pale yellow oil. 250 MHz 1H-nmr (CDCl3) δ (ppm): 2.65 (s, 3H) (—SCH3), 6.95 (s, 1H) (═CHAr), 7.25-7.4 (m, 3H) (ArH), 7.65 (m, 1H) (ArH), 8.85 (s, 1H) (ArH); m/z (M+H)+. 305, HPLC purity 100%, HPLC retention time 3.66 min.

Workup

  1. customprepared in a manner similar to
  2. customirradiated to 120° C. for 45 min
  3. customThe mixture was evaporated in vacuo to dryness
  4. customthe residual oil was purified by flash column chromatography over silica using
  5. additiona 3:7 mixture of hexane and dichloromethane as eluant
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-b9234d13812b45dfa6a4fb3bf48f26ff
Source dataset
uspto-grants-2011_11
Patent number
US08058283B2

Reaction notes

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