Dimethylformamide → HCID 11849611, compound

HRID 1930498Notes

Reaction equation

[C:1](O)(=O)[CH3:2].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3O[C:23]([C:25]([NH2:27])=N)=[CH:22][CH:21]=3)=[CH:16]C=2)=[CH:10][CH:9]=1)(=[NH:7])N.C[N:29](C=O)C>>[C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([C:25]#[N:27])=[CH:2][CH:1]=3)=[CH:16][N:29]=2)=[CH:12][CH:13]=1)#[N:7]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 11849765HCID 11849765, compound

Product 1

HCID 11849611HCID 11849611, compound

Procedure

2-Chloro-5-bromopyrimidine and p-cyanophenylboronic acid were reacted under the above-mentioned Suzuki coupling conditions to give the target dinitrile. Yield 91%, mp 305-306.5° C. (DMF). 1H NMR (DMSO-d6): δ 7.98-8.07 (m, 6H), 8.58 (s, 2H), 9.34 (s, 2H). 13C NMR (DMSO-d6): δ 161.1, 155.5, 140.4, 137.8, 132.6, 132.3, 129.9, 128.0, 127.4, 118.06, 118.00, 113.0, 111.3. MS (ESI) m/e (rel. int.): 282 (M+, 100), 141 (10), 127 (80).

Sources & evidence

ORD record: ord-971a6d5ab577465988dfae0ec6e95c0c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188121B2

Reaction notes

Loading…