4-Methoxybenzylamine → HCID 86699674, compound

HRID 1487176Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([Cl:15])[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:15])[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([NH:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 2-(2,4,6-trichloropyrimidin-5-yl)acetate (from Intermediate A1, 200 mg, 0.74 mmol) in N,N′-dimethylformamide (5 mL) was added (4-methoxyphenyl)methanamine (112 mg, 0.82 mmol) and N,N′-diisopropylethylamine (115 mg, 0.89 mmol). The resulting mixture was stirred at 60° C. for 1 hour, quenched by water and then extracted with ethyl acetate. The organic phases were combined, washed by diluted hydrochloric acid (1 N), water and brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product ethyl 2-(2,4-dichloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 7.26-7.28 (m, 2H), 6.88-6.90 (dd, 2H, J=2.0 Hz, 6.4 Hz), 6.15 (s, 1H), 4.60-4.62 (d, 2H, J=5.2 Hz), 4.11-4.16 (q, 2H, J=7.2 Hz), 3.81 (s, 3H), 3.60 (s, 2H), 1.21-1.26 (t, 3H, J=6.4 Hz).

Workup

customquenched by water
extractionextracted with ethyl acetate
washwashed by diluted hydrochloric acid (1 N), water and brine
dry with materialdried over anhydrous sodium sulfate
customevaporated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-5f9bbff6527f4aca86f55d4cec070dd1
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428508B2

Reaction notes

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