Dimethylamine, hydrochloride → 2-(Dimethylamino)-6-(2-methoxyphenyl)pyrimidine-4-carboxamide

HRID 68295Notes

Reaction equation

HRID 68295 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13](S(C)=O)[N:12]=[C:11]([C:18]([NH2:20])=[O:19])[CH:10]=1.C[CH2:22][N:23](C(C)C)[CH:24](C)C.Cl.CNC>O1CCOCC1>[CH3:22][N:23]([CH3:24])[C:13]1[N:12]=[C:11]([C:18]([NH2:20])=[O:19])[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:14]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 67140270HCID 67140270, compound

Product 1

HCID 156044722-(Dimethylamino)-6-(2-methoxyphenyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

6-(2-Methoxyphenyl)-2-(methylsulfinyl)pyrimidine-4-carboxamide (46 mg, 0.15 mmol), 1,4-dioxane (2 mL), DIPEA (80 μL, 0.45 mmol), and dimethylamine hydrochloride (26 mg, 0.3 mmol) were added to a vial (8 mL). The vial was sealed and heated at 85° C. for two days. After the reaction solution cooled to room temperature, the solvent was removed under vacuum in a Savant SpeedVac. The resulting residue was purified by Prep. HPLC. 1H NMR (300 MHz, CDCl3) δ 7.95 (q, J=7.8, 1.8 Hz, 1H), 7.88 (s, 1H), 7.77 (bs, 1H), 7.40 (m, 1H), 7.04 (t, J=9.0 Hz, 1H), 6.98 (d, J=6.0 Hz, 1H), 5.78 (bs, 1H), 3.92 (s, 3H), 3.26 (s, 6H). HPLC ret. time 2.76 min, 10-100% CH3CN, 5 min gradient; ESI-MS m/z 273.1 (M+H)+.

Workup

  1. customThe vial was sealed
  2. temperatureAfter the reaction solution cooled to room temperature
  3. customthe solvent was removed under vacuum in a Savant SpeedVac
  4. customThe resulting residue was purified by Prep
  5. customHPLC ret. time 2.76 min, 10-100% CH3CN, 5 min gradient

Sources & evidence

ORD record
ord-18a8c311d6674535bedfabff52ff4e17
Source dataset
uspto-grants-2014_09
Patent number
US08822451B2

Reaction notes

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