Trifluoroacetic acid methylene chloride → 6-ethyl-2-imino-3-methyl-tetrahydropyrimidin-4 (1H)-one

HRID 73265Notes

Reaction equation

HRID 73265 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][CH:5]([CH3:9])[NH:4][C:3]1=[N:10]C(=O)[O-].[C:14](O)(C(F)(F)F)=O.C(Cl)Cl>>[CH2:9]([CH:5]1[NH:4][C:3](=[NH:10])[N:2]([CH3:1])[C:7](=[O:8])[CH2:6]1)[CH3:14]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 178429346HCID 178429346, compound

Product 1

HCID 1784369486-ethyl-2-imino-3-methyl-tetrahydropyrimidin-4 (1H)-one

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-10e44f16699f41e5bb673986abc158d7
Source dataset
uspto-grants-2014_09
Patent number
US08829036B2

Reaction notes

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