3-Amino-5-tert-butylselenophene-2-carboxamide → HCID 86698300, compound

HRID 2408984Notes

Reaction equation

HRID 2408984 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH2:11][CH3:12])=[C:9]([CH3:13])[Se: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[Se:8][C:9]=1[CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 866468893-Amino-5-tert-butylselenophene-2-carboxamideHCID 86698281DMF NaOHHCID 86698298HCID 86698298, compound

Product 1

HCID 86698300HCID 86698300, compound

Procedure

The reaction of 4-chloro-5-ethyl-6-methylselenopheno[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 a pale yellow color solid, mp 258-260° C. IR (KBr) vmax 3321, 3149, 2960, 1666, 1582, 1384, 1356, 1224, 1187, 1129, 1042, 1020, 925, 838, 810 cm−1; 1H NMR (400 MHz, CDCl3): δ 10.96 (1H, s, exchangeable with D2O), 8.51 (1H, s), 8.49 (1H, s), 5.44 (2H, br s, exchangeable with D2O), 3.13 (2H, q, J=7.6 Hz), 2.57 (3H, s), 1.44 (9H, s), 1.24 (3H, t, J=7.6 Hz); 13C NMR (100 MHz, CDCl3): δ 172.1, 167.9, 167.1, 153.4, 151.2, 146.9, 135.6, 133.4, 122.8, 120.8, 110.6, 37.0, 32.6, 21.8, 15.8, 15.3; LC-MS (negative ion mode): m/z 465, 467, 469 (M−H)−.

Sources & evidence

ORD record
ord-b88687c96a2943eb9308781dc1a5591a
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

Loading…