4-Chloro-5-ethyl-6-methylthieno[2,3-d]pyrimidine → 3-(5-Ethyl-6-methylthiopheno[2,3-d]pyrimidin-4-ylamino)-5-tert-butylselenophene-2-carboxamide
Reaction equation
Cl[C:2]1[C:3]2[C:10]([CH2:11][CH3:12])=[C:9]([CH3:13])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:14][C:15]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[Se:17][C:16]=1[C:24]([NH2:26])=[O:25].CN(C=O)C.[OH-].[Na+]>>[CH2:11]([C:10]1[C:3]2[C:2]([NH:14][C:15]3[CH:19]=[C:18]([C:20]([CH3:23])([CH3:21])[CH3:22])[Se:17][C:16]=3[C:24]([NH2:26])=[O:25])=[N:7][CH:6]=[N:5][C:4]=2[S:8][C:9]=1[CH3:13])[CH3:12]Participants
4
Procedure
The reaction of 4-chloro-5-ethyl-6-methylthieno[2,3-d]pyrimidine with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound as an off-white color solid, mp 234-236° C. IR (KBr) vmax 3332, 3154, 2962, 1665, 1585, 1362, 1221, 1048, 927, 838, 778 cm−1; 1H NMR (400 MHz, CDCl3): δ 11.04 (1H, s, exchangeable with D2O), 8.64 (1H, s), 8.56 (1H, s), 5.34 (2H, br s, exchangeable with D2O), 3.15 (2H, q, J=7.5 Hz), 2.49 (3H, s), 1.45 (9H, s), 1.25 (3H, t, J=7.6 Hz); 13C NMR (100 MHz, CDCl3): δ 168.0, 167.3, 167.0, 152.7, 151.7, 146.9, 131.0, 130.9, 122.8, 117.7, 110.6, 37.1, 32.5, 20.8, 15.6, 13.4; LC-MS (negative ion mode): m/z 419, 421 (M−H)−.
Sources & evidence
- ORD record
- ord-cf313b8f2be6445885b7f0c76878f40b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815879B2
Reaction notes
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