4-Methoxybenzylamine → HCID 24826685, compound

HRID 2102835Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[C:5]2[O:10][C:9]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:8]=3[C:6]=2[N:7]=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>N1C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][C:5]3[C:4]([N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[N:3][C:2]([NH:30][CH2:29][C:28]4[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)=[N:7][C:6]=3[C:8]=2[CH:14]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 2,8-dichloro-4-(4-methyl-piperazin-1-yl)-benzo[4,5]furo[3,2-d]pyrimidine (1.3 g, 3.0 mmol) in pyridine (4 mL) was added 4-methoxybenzylamine (4 mL, 30 mmol). After heating at 200° C. for 1 h in the microwave, the resulting mixture was concentrated and the residue was purified by FCC (CH2Cl2/MeOH) to give [8-chloro-4-(4-methyl-piperazin-1-yl)-benzo[4,5]furo[3,2-d]pyrimidin-2-yl]-(4-methoxy-benzyl)-amine. The intermediate was then dissolved in TFA (7 mL) and heated at 65° C. for 3 h. The mixture was diluted with CH2Cl2 (20 mL) and H2O (20 mL). The product was extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with 1 N NaOH (20 mL), dried, and concentrated. The residue was purified by reverse-phase chromatography to afford the desired product (523 mg, 55%). MS: 318.1. 1H NMR (CDCl3): 7.99 (d, J=1.99 Hz, 1H), 7.48-7.47 (m, 2H), 4.76 (s, 2H), 4.08-4.06 (m, 4H), 2.57-2.55 (m, 4H), 2.37 (s, 3H).

Workup

concentrationthe resulting mixture was concentrated
customthe residue was purified by FCC (CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-0867c0fe505b47689bbaa1261a84e749
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576092B2

Reaction notes

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