Methyl iodide → HCID 22278815, compound

HRID 1063266Notes

Reaction equation

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

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 6340Iodoethane

HCID 22278698HCID 22278698, compound

Product 1

HCID 22278815HCID 22278815, compoundYield 87%

Procedure

Following the general procedure of Example 13 Step 3 and making non-critical variations but substituting (2S)-2-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]butan-1-ol with 3-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}butan-1-ol (Example 39, 95 mg, 0.24 mmol) and iodoethane with iodomethane the reaction was carried out and gave 108 mg of a crude yellow oil. This material was purified by Biotage MPLC (40 g column, 20% ethyl acetate in heptane) to give 85 mg (87%) of 3,6-diethyl-N-(3-methoxy-1-methylpropyl)-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine as a clear oil. Rf 0.30 (5% acetone in toluene). IR (liq.) 2965, 2933, 2873, 1567, 1551, 1494, 1465, 1446, 1392, 1248, 1233, 1204, 1197, 1121, 1110 cm−1. OAMS supporting ions at: ESI+398.2.

Workup

customgave 108 mg of a crude yellow oil
customThis material was purified by Biotage MPLC (40 g column, 20% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-54a1439fbecf49c79afe631c145a7ef2
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964965B2

Reaction notes

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