Veratrylamine → N-(3,4-dimethoxybenzyl)-7-(2-fluorobenzyl)4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine

HRID 1817177

Reaction equation

Cl[C:2]1[N:3]=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:6]=2[N:7]=1.[CH2:24]([NH2:35])[C:25]1[CH:34]=[CH:33][C:30]([O:31][CH3:32])=[C:27]([O:28][CH3:29])[CH:26]=1>CN1CCCC1=O>[CH3:29][O:28][C:27]1[CH:26]=[C:25]([CH:34]=[CH:33][C:30]=1[O:31][CH3:32])[CH2:24][NH:35][C:2]1[N:3]=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-chloro-7-(2-fluorobenzyl)-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine (254 mg, 0.78 mmol) in N-methylpyrrolidone (2 mL) was treated with veratrylamine (0.25 mL, 1.66 mmol), heated to 100° C. for 16 h and purified by chromatography (Heptane:EtOAc, 4:1) to give the title compound (316 mg, 88%) as a cream solid.

Workup

custompurified by chromatography (Heptane:EtOAc, 4:1)

Sources & evidence

ORD record: ord-1c36fde3337d4a65b799365dc4a52858
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598256B2

Linked notes

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