Water → 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile

HRID 1677271Notes

Reaction equation

I[C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.[C:22]([Cu])#[N:23].O>CN(C=O)C>[NH2:14][C:11]1[N:10]=[C:9]([NH2:15])[C:8]([O:7][C:6]2[C:5]([CH:17]([CH3:19])[CH3:18])=[CH:4][C:3]([O:20][CH3:21])=[C:2]([CH:16]=2)[C:22]#[N:23])=[CH:13][N:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.37 g, 0.925 mmol) and CuCN (0.12 g, 1.39 mmol) in DMF (5 ml) was heated at 120° C. for 3 hours. Water (100 ml) was added, and the precipitate was collected. The residue was triturated with methanolic dichloromethane (10% CH3OH in CH2Cl2 with 0.1% NH4OH) to release the product from its copper complex and filtered. The filtrate was concentrated and purified via flash chromatography (3% CH3OH in CH2Cl2 with 0.1% NH4OH) to give 5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile as white solid (0.12 g, 44%): M+H 300.

Workup

customthe precipitate was collected
customThe residue was triturated with methanolic dichloromethane (10% CH3OH in CH2Cl2 with 0.1% NH4OH)
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified via flash chromatography (3% CH3OH in CH2Cl2 with 0.1% NH4OH)

Sources & evidence

ORD record: ord-3357b223863d40b2a97368cfc400840d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008313B2

Reaction notes

Loading…