4-Methylmorpholine → 2-Diethylamino-6-(2,6-dimethoxy-phenyl)-pyrimidine-4-carboxylic acid amide

HRID 68304Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15](S(C)(=O)=O)[N:14]=[C:13]([C:21]([NH2:23])=[O:22])[CH:12]=1.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].CN1CCOCC1>CS(C)=O>[CH2:24]([N:26]([CH2:27][CH3:28])[C:15]1[N:14]=[C:13]([C:21]([NH2:23])=[O:22])[CH:12]=[C:11]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=2[O:9][CH3:10])[N:16]=1)[CH3:25]

Participants

Conditions

Temperature: 75 °C

Procedure

A 4 mL screw-cap vial was charged with a solution of 6-(2,6-dimethoxy-phenyl)-2-methanesulfonyl-pyrimidine-4-carboxylic acid amide (assumed 0.3 mmol) in DMSO (0.9 mL). A solution of diethylamine and N-methyl-morpholine (NMM) in DMSO (0.3 mL, 3 M in both, 0.9 mmol, 3 eq.) was added, and the sealed vial was heated at 75° C. for 22 hours. The mixture was then submitted for purification by preparative HPLC to afford 18 mg (18%) of the 2-diethylamino-6-(2,6-dimethoxy-phenyl)-pyrimidine-4-carboxylic acid amide. 1H NMR (300 MHz, CDCl3) □ 7.79 (br s, 1H), 7.30 (t, J=8.3 Hz, 1H), 7.26 (s, 1H), 6.61 (d, J=8.3 Hz, 2H), 6.16 (brs, 1H), 3.74 (s, 6H), 3.66 (q, J=6.9 Hz, 4H), 1.22 (t, J=6.9 Hz, 6H); HPLC ret. time 2.85 min., 10-100% CH3CN, 5 min gradient; ESI-MS m/z 330.2 (M+H)+.

Workup

customA 4 mL screw-cap vial
customThe mixture was then submitted for purification by preparative HPLC

Sources & evidence

ORD record: ord-748b502442154eae8909089aecb094e4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822451B2

Reaction notes

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