Benzenamine, 3-ethynyl- → 4-(3-Ethynyl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic Acid

HRID 1937400Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:14][C:15]1[CH:16]=[C:17]([C:21]#[CH:22])[CH:18]=[CH:19][CH:20]=1>CO>[C:21]([C:17]1[CH:16]=[C:15]([NH:14][C:2]2[C:3]3[C:10]([C:11]([OH:13])=[O:12])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:20]=[CH:19][CH:18]=1)#[CH:22]

Participants

Conditions

Temperature: 125 °C

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (0.38 g, 1.9 mmol) in dry methanol (4ml) was added m-aminophenyl acetylene (0.47 g, 4.0 mmol). The suspension was heated in a sealed pressure tube at 125° C. for 18 hours. The reaction mixture was cooled to ambient temperature, filtered with methylene chloride washes and dried in vacuo to afford the title compound as a tan powder (0.30 g, 54%). TS-MS: 278 (MH+); anal. RP18-HPLC RT: min.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
filtrationfiltered with methylene chloride washes
customdried in vacuo

Sources & evidence

ORD record: ord-f987ca14dee448e7b92f7eca08afe04e
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395733B1

Reaction notes

Loading…