Tetrahydrofuran → HCID 18980280, compound

HRID 1489043Notes

Reaction equation

HRID 1489043 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[NH:22][CH2:23][CH2:24][CH2:25][NH2:26].[O-2:27].[Ca+2].[O:29]1CCCC1>>[C:13]([OH:14])(=[O:29])[C:12]([OH:11])=[O:27].[O:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:26][CH2:25][CH2:24][CH2:23][NH:22][C:17]3[N:16]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:15]=2[O:14][CH2:13][CH2:12]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 6850728CalciumoxideHCID 14397405N-(3-aminopropyl)pyrimidin-2-amineHCID 18980288HCID 18980288, compound

Product 1

HCID 18980280HCID 18980280, compoundYield 36%

Conditions

Temperature
160 °C

Procedure

A mixture of 5-(3-chloropropoxy)-2,3-dihydro-1,4-benzodioxin (0.017 mol), N-2-pyrimidinyl-1,3-propanediamine (0.026 mol) and calcium oxide (5 g) in tetrahydrofuran (150 ml) was stirred overnight at 160° C. (pressure vessel). The mixture was cooled, filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3)95/5). The pure fractions were collected and the solvent was evaporated, yielding 2.66 g N-[3-[(2,3-dihydro-1,4-benzodioxin-5-yl)oxy]propyl]-N'-2-pyrimidinyl-1,3-propanediamine ethanedioate(1:1) (36.0%); mp. 200.2° C. (comp. 8)

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3)95/5)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-03568a1a619c4f01a2fb82f31c841667
Source dataset
uspto-grants-1997_10
Patent number
US05677310

Reaction notes

Loading…