3-Amino-5-tert-butylselenophene-2-carboxamide → HCID 86698294, compound

HRID 2408979Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:15][C:16]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[Se:18][C:17]=1[C:25]([NH2:27])=[O:26].CN(C=O)C.[OH-].[Na+]>>[C:11]([C:9]1[O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:15][C:16]3[CH:20]=[C:19]([C:21]([CH3:24])([CH3:22])[CH3:23])[Se:18][C:17]=3[C:25]([NH2:27])=[O:26])[C:3]=2[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 3

HCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

HCID 86698281DMF NaOH

HCID 86698293HCID 86698293, compound

Product 1

HCID 86698294HCID 86698294, compound

Procedure

The reaction of 4-chloro-6-tert-butylfuro[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 288-290° C. IR (KBr) vmax 3491, 3325 2964, 1593, 1388, 1354, 1314, 1287, 1149, 1119, 1089, 936, 806, 773 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 10.80 (1H, s, exchangeable with D2O), 8.46 (2H, s), 7.48 (2H, br s, exchangeable with D2O), 6.41 (1H, s), 1.39 (9H, s), 1.36 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 167.4, 167.1, 166.0, 164.1, 152.6, 152.3, 144.9, 121.0, 113.1, 103.3, 94.8, 36.4, 32.7, 32.2, 28.23; LC-MS (negative ion mode): m/z 417, 419 (M−H)−.

Sources & evidence

ORD record: ord-7ddba5735f6a4b9baa7f475557ade917
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

Loading…