1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride → HCID 178429401, compound

HRID 2069361Notes

Reaction equation

HRID 2069361 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.[NH2:16][C:17]1[N:22]=[C:21]([OH:23])[CH:20]=[C:19]([CH3:24])[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:16][C:17]4[N:22]=[C:21]([OH:23])[CH:20]=[C:19]([CH3:24])[N:18]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chlorideHCID 178429408HCID 178429408, compound

Product 1

HCID 178429401HCID 178429401, compound

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 2-amino-6-methylpyrimidin-4-ol (25 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. 313.1, found 314.1 (M+1)+. Retention time 2.31 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-9494d503e0a84c91a822073f8f1ff3d1
Source dataset
uspto-grants-2012_10
Patent number
US08299099B2

Reaction notes

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