Ethanol → HCID 178494134, compound

HRID 474873Notes

Reaction equation

HRID 474873 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH2:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26][C:27]2[C:28](=[O:35])[N:29]=[C:30](SC)[NH:31][CH:32]=2)=[CH:22][N:21]=1.[CH2:36](O)C>>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([CH3:36])[C:30]3[NH:31][CH:32]=[C:27]([CH2:26][C:23]4[CH:22]=[N:21][C:20]([O:19][CH3:18])=[N:25][CH:24]=4)[C:28](=[O:35])[N:29]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 209919212-[4-(4-Fluorophenoxy)phenyl]ethan-1-amineHCID 178494160HCID 178494160, compound

Product 1

HCID 178494134HCID 178494134, compoundYield 19%

Conditions

Temperature
125 °C

Procedure

2-[4-(4-fluoro-phenoxy)-phenyl]ethylamine (0.204 mmol, 1 eq) and 5-(2-methoxy-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (0.082 mmol, 0.4 eq) were dissolved in dry ethanol (200 μL) and stirred at 125° C. for 16 hours. Solvent was evaporated and crude product was purified by Waters Mass Direct Autopurification system giving 2-({2-[4-(4-fluoro-phenoxy)phenyl]-ethyl}-methyl-amino)-5-(2-methoxy-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (0.039 mmol, yield: 19%, HPLC-MS/UV: [M+H]+=462.24; rt: 10.59 min; purity: 99%). 1H NMR (300 MHz; CDCl3) δ/ppm 2.85 (t, J=7.17, 2H), 2.98 (s, 2H), 3.51 (s, 2H), 3.73 (t, J=6.72, 2H), 3.95 (s, 3H), 6.85-7.05 (m, 5H), 7.11-7.17 (m, 2H), 7.23-7.28 (m, 1H), 7.65 (s, 1H), 8.37 (s, 1H), 10.09 (br.s., 1H)

Workup

  1. customSolvent was evaporated
  2. customcrude product was purified by Waters Mass Direct Autopurification system

Sources & evidence

ORD record
ord-5bc2032ec8564712a5079d492f273ca7
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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