Ethanol → 4-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile

HRID 2274117Notes

Reaction equation

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

Participants

Reactant 4

HCID 702Ethanol

HCID 81531Diisopropylethylamine

HCID 122782624-Amino-6-chloropyrimidine-5-carbonitrile

HCID 866669161-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine

Product 1

HCID 867114694-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrileYield 54%

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine (40 mg, 0.14 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (J & W PharmLab, #70-0156 33 mg, 0.21 mmol) and N,N-diisopropylethylamine (74 μL, 0.43 mmol) in ethanol (1.6 mL, 27 mmol) was heated at 100° C. overnight. Purification by preparative LC/MS (pH10) gave the desired compound (54% yield). LCMS calculated for C14H13BrClFN5O (M+H)+: m/z=400.0, 402.0. found: 400.0, 402.0. 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 1H), 7.77 (m, 1H), 7.28 (br s, 2H), 5.56 (m, 1H), 3.92 (s, 1H), 1.40 (m, 3H).

Workup

customPurification by preparative LC/MS (pH10)

Sources & evidence

ORD record: ord-22d9501d5b304e4baa3ea742a925fb54
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126948B2

Reaction notes

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