Epichlorohydrin → HCID 3438781, compound

HRID 1047095Notes

Reaction equation

HRID 1047095 reaction equation
[Na].[CH3:2][N:3]1[C:11]2[N:10]=[CH:9][N:8]([CH2:12]C3C=CC=CC=3)[C:7]=2[C:6](=[O:19])[NH:5][C:4]1=[O:20].[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>>[O:25]1[CH2:24][CH:23]1[CH2:21][N:5]1[C:6](=[O:19])[C:7]2[N:8]([CH3:12])[CH:9]=[N:10][C:11]=2[N:3]([CH3:2])[C:4]1=[O:20]

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 6856307-Benzyl-3-methylxanthineHCID 5360545Sodium

Product 1

HCID 3438781HCID 3438781, compound

Procedure

and R═R1═CH3). A suspension of 3 g (0.148 mole) of the sodium salt of 3,7-dimethylxanthine (III, 1-Na salt; R═R1═CH3) and 20 mL of epichlorhydrin is heated while stirring at 65-70° for 20 hours. After cooling, the precipitate is filtered out and washed with methylene chloride. The derived solution of IX in methylene chloride is stripped and the grease-like residue is kneaded in absolute ether, yielding 2.7 (77%) of 1-(2,3-epoxypropyl)-3,7-dimethylxanthine, melting point 115-119°, M+ 236 (J-C. Pascal et al, J. Med. Chem., 1985, No. 28, No. 5, pp. 647-652, melting point 116-117°).

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered out
  4. washwashed with methylene chloride

Sources & evidence

ORD record
ord-98bb3bdff2c948229636cccffd622d42
Source dataset
uspto-grants-2013_10
Patent number
US08569489B2

Reaction notes

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