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

HRID 1789939Notes

Reaction equation

HRID 1789939 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][C:33]([CH3:38])([CH2:36][OH:37])[CH2:34][OH:35]>CN1C=CN=C1>[NH2:31][C:15]1[N:14]=[C:13]2[C:18]([C:19]([NH:32][C:33]([CH3:38])([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

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 220370392,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7-pteridinamine

Product 1

HCID 101583542-[[7-Amino-2-[[(2,3-difluorophenyl)methyl]thio]-4-pteridinyl]amino]-2-methyl-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 13901-MethylimidazoleSolvent

Procedure

A solution of the product from example 1, step (c) (0.25 g) and 2-amino-2-methyl-1,3-propanediol (0.28 ml) in N-methylimidazole (1 ml) was heated in a microwave at 160° C. for 95 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 oil which was purified by silica gel flash column chromatography, eluting with 10:1 dichloromethane:methanol to give the title compound as a pale brown solid (0.031 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 oil which
  7. customwas purified by silica gel flash column chromatography
  8. washeluting with 10:1 dichloromethane

Sources & evidence

ORD record
ord-b1480fa09b40490e844336d04e3d4254
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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