Neopentylamine → HCID 66956070, compound

HRID 1399759Notes

Reaction equation

HRID 1399759 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[CH2:24]([NH2:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C(O)(C)C>[CH3:8][C:6]1[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=[C:2]([NH:29][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:7]=1

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 66956070HCID 66956070, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.300 mmol), and neopentyl amine (0.177 mL; 1.502 mmol) were placed in a 2 mL reaction tube and dissolved in isopropanol (1.5 mL). The tube was sealed and irradiated in a microwave oven at 180° C. for 1 h. The reaction mixture was partitioned between brine and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 57 mg (49%) of the title compound as a colorless oil.

Workup

  1. customThe tube was sealed
  2. customirradiated in a microwave oven at 180° C. for 1 h
  3. customThe reaction mixture was partitioned between brine and dichloromethane
  4. filtrationfiltered over a phase separator
  5. filtrationfilter (1PS)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane

Sources & evidence

ORD record
ord-926f9f4ceb6f4e26ae77c2f981680c61
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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