4-Chloro-6-phenylfuro[2,3-d]pyrimidine → 3-(6-Phenylfuro[2,3-d]pyrimidin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

HRID 2408977Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[Se:20][C:19]=1[C:27]([NH2:29])=[O:28].CN(C=O)C.[OH-].[Na+]>>[C:11]1([C:9]2[O:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:17][C:18]4[CH:22]=[C:21]([C:23]([CH3:26])([CH3:24])[CH3:25])[Se:20][C:19]=4[C:27]([NH2:29])=[O:28])[C:3]=3[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidine

HCID 86646889HCID 86646889, compound

HCID 86698281DMF NaOH

Product 1

HCID 866982923-(6-Phenylfuro[2,3-d]pyrimidin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

Procedure

The reaction of 4-chloro-6-phenylfuro[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 280-282° C. IR (KBr) v. 3326, 3188, 2953, 1624, 1386, 1358, 1324, 1283, 1150, 1089, 1016, 921, 822, 778, 755 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 11.94 (1H, s, exchangeable with D2O), 8.53 (1H, s), 8.50 (1H, s), 7.96 (2H, d, J=7.2 Hz), 7.43-7.55 (5H, m), 7.32 (1H, s), 1.40 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 167.4, 167.1, 166.2, 153.3, 152.5, 152.3, 144.7, 129.3, 129.1, 128.6, 124.7, 121.1, 113.3, 104.4, 97.4, 36.4, 32.2; LC-MS (negative ion mode): m/z 437, 439 (M−H)−.

Sources & evidence

ORD record: ord-ff4588497f8743c39b2a800aacb6daef
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

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