4-Chloropyrido[2,3-d]pyrimidine → 5-tert-Butyl-3-(pyridino[2,3-d]pyrimidin-4-ylamino)selenophene-2-carboxamide

HRID 2408971Notes

Reaction equation

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

Participants

Reactant 3

HCID 5690394-Chloropyrido[2,3-d]pyrimidine

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

HCID 86698281DMF NaOH

Product 1

HCID 866982745-tert-Butyl-3-(pyridino[2,3-d]pyrimidin-4-ylamino)selenophene-2-carboxamide

Procedure

The reaction of 4-chloropyridino[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 yellow color solid, mp 222-224° C. IR (KBr) vmax 3310, 3180, 2961, 1616, 1572, 1383, 1332, 1316, 1280, 1245, 1226, 1090 cm−1; 1H NMR (400 MHz, CDCl3+DMSO-d6): δ 9.10 (1H, dd, J=4.4, 1.6 Hz), 8.96 (1H, s), 8.81 (1H, s), 8.55 (1H, dd, J=8.4, 1.6 Hz), 7.54 (1H, dd, J=8.4, 4.4 Hz), 6.50 (2H, br s), 1.48 (9H, s); 13C NMR (100 MHz, CDCl3+DMSO-d6): 168.6, 168.3, 158.6, 157.9, 156.5, 155.8, 146.1, 131.3, 121.9, 121.1, 111.7, 110.3, 36.8, 32.2; LC-MS (negative ion mode): m/z 372, 374 (M−H)−.

Sources & evidence

ORD record: ord-61246631637b4ab09245fbc494844180
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

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