2,6-Dimethoxy-4-aminopyrimidine → 1-(benzo[d][1,3]dioxol-5-yl)-N-(2,6-dimethoxypyrimidin-4-yl)cyclopropanecarboxamide

HRID 1524832Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:16][O:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[C:20]([O:25][CH3:26])[N:19]=1>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:24][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[N:19]=[C:18]([O:17][CH3:16])[N:23]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 115 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.2 mmol) in pyridine (2 mL) was added 2,6-dimethoxypyrimidin-4-amine (31 mg, 0.2 mmol) and the reaction mixture was stirred at 115° C. for 15 hours. The solvent was evaporated to dryness and the residue redissolved in DMF, filtered and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 343.3. Found 344.1 (M+1)+. Retention time 2.87 minutes.

Workup

customThe solvent was evaporated to dryness
dissolutionthe residue redissolved in DMF
filtrationfiltered
custompurified by reverse-phase preparative liquid chromatography
customto yield the pure product

Sources & evidence

ORD record: ord-3f186051d4bc40b88481b075152a2fdf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079916B2

Reaction notes

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