Water → HCID 59514516, compound

HRID 2422157Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:6](Cl)=[N:7][C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[N:9][C:10]=1[N:11]([CH3:13])[CH3:12].[Cl-].[CH3:27][NH2+:28][CH3:29].C(N(CC)C(C)C)(C)C.O>CN1C(=O)N(C)CCC1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:6]([N:28]([CH3:29])[CH3:27])=[N:7][C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[N:9][C:10]=1[N:11]([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl[4-chloro-6-(dimethylamino)-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (7.75 g, 21.25 mmol), dimethylammonium chloride (5.20 g, 63.74 mmol), and N,N-diisopropylethylamine (10.98 g, 84.98 mmol) in DMPU (50 mL) was heated at 150° C. in a sealed tube for 15 hours. After cooling to room temperature, the dark mixture was poured into water and extracted with ethyl acetate. The combined extracts were washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield the crude product as a dark oil. Chromatographic purification of this crude product over silica gel eluting with 25% ethyl acetate in n-hexane containing 0.1% triethylamine gave methyl[4,6-bis(dimethylamino)-2-(4-nitro-benzyl)pyrimidin-5-yl]acetate (5.44 g, 69%) as a red colored oil.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe combined extracts were washed sequentially with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customto yield the crude product as a dark oil
customChromatographic purification of this crude product over silica gel eluting with 25% ethyl acetate in n-hexane containing 0.1% triethylamine

Sources & evidence

ORD record: ord-6a6f75eccee749a9b18c7c3918feb24b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960393B2

Reaction notes

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