HCID 22020948, compound → HCID 22020967, compound

HRID 1793336Notes

Reaction equation

HRID 1793336 reaction equation
CS(O[CH2:6][CH:7]1[O:15][C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[O:8]1)(=O)=O.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][NH:22][C:21]1=[O:28]>>[O:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[O:15][CH:7]1[CH2:6][NH:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][C:24]([CH3:26])([CH3:27])[CH2:23][NH:22][C:21]1=[O:28]

Participants

3

Reactant 2

HCID 22020948HCID 22020948, compoundHCID 22020971HCID 22020971, compound

Product 1

HCID 22020967HCID 22020967, compoundYield 50.2%

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate (6) (0.0092 mol) and intermediate (13) (0.0183 mol) was stirred for 2 hours at 100° C. The crude reaction mixture was purified by open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10). The desired fractions were collected and the solvent was evaporated. The residue was washed with DIPE, then dried, yielding 1.48 g of (±)-1-[3-[(1,3-dioxolo[4,5-b]pyridin-2-ylmethyl)amino]-propyl]tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone (compound 10).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10)
  3. customThe desired fractions were collected
  4. customthe solvent was evaporated
  5. washThe residue was washed with DIPE
  6. customdried

Sources & evidence

ORD record
ord-b9164710d6a9432fba83d9bfa12c024f
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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