Serinol → 2-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediol

HRID 1789938Notes

Reaction equation

HRID 1789938 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:20]=[C:19](SCC2C=CC=C(F)C=2F)[C:18]2[C:13](=[N:14][C:15]([NH2:31])=[CH:16][N:17]=2)[N:12]=1.[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35]>CN1C=CN=C1>[NH3:12].[NH2:31][C:15]1[N:14]=[C:13]2[C:18]([C:19]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[N:20][C:11]([S:10][CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[N:12]2)=[N:17][CH:16]=1

Participants

5

Reactant 2

HCID 68294SerinolHCID 220370392,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7-pteridinamine

Product 2

HCID 222AmmoniaHCID 102719362-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-1,3-propanediolYield 39.2%

Reagents, catalysts & solvents 1

HCID 13901-MethylimidazoleSolvent

Procedure

A solution of the product from example 1, step (c) (0.12 g) and serinol (330 mg) in 1-methylimidazole (1 ml) was heated at 130° C. for 90 minutes. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to give a brown solid which was purified by silica gel flash column chromatography, eluting with 200:20:1 dichloromethane:methanol:880 ammonia solution, to give the title compound as a pale brown solid (0.02 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown solid which
  7. customwas purified by silica gel flash column chromatography
  8. washeluting with 200:20:1 dichloromethane

Sources & evidence

ORD record
ord-f99cb156d7224367b03f8c191091bbb7
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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