2-Aminothiophenol → HCID 59516512, compound

HRID 1160436Notes

Reaction equation

CO[C:3]1[C:8]([C:9]([C:11](=[C:17]([S:20][CH3:21])SC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:7][N:6]=[C:5]([S:22][CH3:23])[N:4]=1.[NH2:24][C:25]1C=[CH:29][CH:28]=[CH:27][C:26]=1S.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C1(C)C=CC=CC=1.O>[CH2:15]([O:14][C:12]([C:11]1[C:9](=[O:10])[C:8]2[CH:7]=[N:6][C:5]([S:22][CH3:23])=[N:4][C:3]=2[N:24]2[C:17]=1[S:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=1)=[O:13])[CH3:16]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of ethyl 2-(4-methoxy-2-(methylthio)pyrimidine-5-carbonyl)-3,3-bis(methylthio)acrylate (475 mg, 1.27 mmol) and 2-aminobenzenethiol (200 mg, 1.60 mmol) in toluene (5 mL) was heated to dryness and continued heating neat at 140° C. for 1 h. Toluene (30 mL) and K2CO3 (350 mg, 2.53 mmol) were added to the reaction and it was heated for an additional 1 h. The reaction mixture was cooled to rt and EtOAc (100 mL) and H2O (50 mL) were added. The layers were separated and the organic layer was washed with brine (100 mL), dried over Na2SO4, and concentrated. The crude solid was triturated in Et2O to afford the desired product as a yellow solid (260 mg, 55%). MS (m/z): 372 (MH+). 1H NMR (DMSO-d6) δ: 9.37 (d, 1H), 9.30 (s, 1H), 8.06 (m, 1H), 7.65 (m, 1H), 7.54 (m, 1H), 4.35 (q, 2H), 2.78 (s, 3H), 1.34 (t, 3H).

Workup

temperaturewas heated for an additional 1 h
temperatureThe reaction mixture was cooled to rt
customThe layers were separated
washthe organic layer was washed with brine (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude solid was triturated in Et2O

Sources & evidence

ORD record: ord-e29429e4853042bc9946f6b4bd6a3890
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816406B2

Reaction notes

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