Water → HCID 118162107, compound

HRID 1749476Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH2:18][CH2:19][NH2:20])[CH:15]=[CH:16][CH:17]=1.CCN(C(C)C)C(C)C.O>C1COCC1.C(OCC)(=O)C>[Cl:8][C:6]1[C:5]([C:9]#[N:10])=[CH:4][N:3]=[C:2]([NH:20][CH2:19][CH2:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([Cl:11])[CH:13]=2)[N:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2,4-dichloropyrimidine-5-carbonitrile (5.0 g, 28.90 mmol), 2-(3-chlorophenyl)ethanamine (4.78 g, 28.9 mmol) and DIEA (7.45 g, 57.8 mmol) in THF (50 mL) was stirred at 50° C. for 3 h. After cooling to room temperature, water (80 mL) was added and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with saturated aqueous ammonium chloride, brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuum to give the crude product, which was treated with ethyl acetate (30 mL) and stirred for 30 min. The mixture was filtered and dried to afford the title compound (3.20 g, 10.92 mmol, 38% yield). MS (ESI) m/z 293.1, 294.1 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
washThe combined organic layers were washed with saturated aqueous ammonium chloride, brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe filtrate was evaporated in vacuum
customto give the crude product, which
stirringstirred for 30 min
filtrationThe mixture was filtered
customdried

Sources & evidence

ORD record: ord-793c60e724c2428fae809360c506e460
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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