Trifluoroacetic acid methylene chloride → HCID 178435248, compound

HRID 2362580Notes

Reaction equation

HRID 2362580 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C@:15]3(C)[CH2:20][C:19](=[O:21])[N:18]([CH3:22])[C:17](=[N:23]C(=O)OC(C)(C)C)[NH:16]3)[CH:12]=[CH:13][CH:14]=2)[C:5]([OH:8])=[CH:6][CH:7]=1.[C:32](O)([C:34](F)(F)F)=O.C(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C@@:15]3([CH2:32][CH3:34])[NH:16][C:17](=[NH:23])[N:18]([CH3:22])[C:19](=[O:21])[CH2:20]3)[CH:12]=[CH:13][CH:14]=2)[C:5]([OH:8])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 178481510HCID 178481510, compound

Product 1

HCID 178435248HCID 178435248, compoundYield 60%

Procedure

(S)-tert-butyl 4-(3-(3-chloro-6-hydroxyphenyl)phenyl)-1,4-dimethyl-6-oxo-tetrahydropyrimidin-2(1H)-ylidenecarbamate (CF3; R1═R6=Me, R21=3-chloro-6-hydroxyphenyl) (23 mg, 0.05 mmol) was treated with 1 mL of 30% TFA/CH2Cl2 at RT for 30 min. The volatiles were removed in vacuo. The residue was redissolved in acetonitrile (5 mL) and evaporated again to afford 17 mg of the crude product as a yellow solid. The crude product was purified via reverse phase HPLC to provide 10 mg (60%) of (S)-6-(3-(3-chloro-6-hydroxy-phenyl)phenyl)-6-ethyl-2-imino-3-methyl-tetrahydropyrimidin-4(1H)-one (CF4; R1═R6=Me, R21=3-chloro-6-hydroxyphenyl) as a white solid. 1HNMR (CDCl3, 300 MHz): 11.4 (br s, 1H), 7.6-4.25 (m, 3H), 7.24-6.84 (m, 3H), 3.68 (br s, 1H), 5.18 (br s, 1H), 3.39 (d, J=16.1 Hz, 1H), 3.20 (s, 3H), 2.95 (d, J=15.8 Hz, 1H), 1.74 (s, 3H). MS (ESI): MH+=344.1. HPLC (A) Rt=5.07 min.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionThe residue was redissolved in acetonitrile (5 mL)
  3. customevaporated again
  4. customto afford 17 mg of the crude product as a yellow solid
  5. customThe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-6979033026a74000b1ad262aed165664
Source dataset
uspto-grants-2014_04
Patent number
US08691833B2

Reaction notes

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