2-Furancarboxylic acid, hydrazide → furan-2-carboxylic acid N'-{2-amino-7-[2-(t-butyldimethylsilanyloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-hydrazide

HRID 2239781Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[N:16]=[C:17]([NH2:21])[N:18]=[C:19](Cl)[C:14]=2[CH:13]=[CH:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]([NH:29][NH2:30])=[O:28]>C(O)CCC>[NH2:21][C:17]1[N:18]=[C:19]([NH:30][NH:29][C:27]([C:23]2[O:22][CH:26]=[CH:25][CH:24]=2)=[O:28])[C:14]2[CH:13]=[CH:12][N:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:15]=2[N:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The title A compound, 7-[2-(t-Butyldimethylsilanyloxy)ethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (100 mg, 0.3 mmol) and 2-furoic acid hydrazide (76 mg, 0.6 mmol) are taken into 3 mL of n-butanol. The mixture is stirred at 120° C. under N2 for 2 h. The solvent is evaporated under vacuum and the residue is purified by flash chromatography using EtOAc/MeOH (95/5) as eluent to give furan-2-carboxylic acid N′-{2-amino-7-[2-(t-butyldimethylsilanyloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-hydrazide: LC/MS (M+1=417). 1H NMR (CDCl3, 400 MHz) δ-0.08 (s, 6H), 0.84 (s, 9H), 3.85 (t, 2H, J=4.8 Hz), 4.12 (t, 2H, J =4.8 Hz), 4.81 (br s, 2H, NH2), 6.26 (d, 1H, J=2.4 Hz), 6.51 (m, 1H), 6.74 (d, 1H, J=2.4 Hz), 7.20 (d, 1H, J=2.8 Hz), 7.27 (d, 1H, J=2.8 Hz), 7.49 (s, 1H).

Workup

customThe solvent is evaporated under vacuum
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-75a28725d1944eea8ece51fc2e4314d2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723343B2

Reaction notes

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