2-Amino-4-methylpyrimidine → 1-(benzo[d][1,3]dioxol-5-yl)-N-(4-methylpyrimidin-2-yl)cyclopropanecarboxamide

HRID 2069362Notes

Reaction equation

HRID 2069362 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][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=1>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:23][C:19]4[N:18]=[C:17]([CH3:16])[CH:22]=[CH:21][N:20]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 79392-Amino-4-methylpyrimidineHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 442065461-(benzo[d][1,3]dioxol-5-yl)-N-(4-methylpyrimidin-2-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 4-methylpyrimidin-2-amine (22 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. 297.3, found 298.3 (M+1)+. Retention time 2.14 minutes.

Workup

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

Sources & evidence

ORD record
ord-8c08bec76abb48bbb5bafcf9c9378128
Source dataset
uspto-grants-2012_10
Patent number
US08299099B2

Reaction notes

Loading…