Hydrochloric Acid → HCID 58016784, compound

HRID 1926907Notes

Reaction equation

HRID 1926907 reaction equation
[OH-].[Na+].[CH3:3][C@@H:4]([OH:8])[C@H:5]([OH:7])[CH3:6].Cl[C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.Cl>C1(C)C=CC=CC=1.COCCOC.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:11]3[C:10]([O:7][C@H:5]([CH3:6])[C@H:4]([OH:8])[CH3:3])=[N:15][CH:14]=[N:13][C:12]=3[O:16][C:17]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 225936(2R,3R)-ButanediolHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 58016784HCID 58016784, compound

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

Add 2.4 ml of a 12.5 N sodium hydroxide solution to a solution of 1.34 g (14.8 mmol) (2R,3R)-butane-2,3-diol in 20 ml toluene, 7 ml 1,2-dimethoxyethane and 7 ml water at 70° C. After adding 101 mg (0.30 mmol) tetra-n-butylammonium hydrogensulphate and 1.00 g (2.97 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture for 17 h at 70° C. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract three times with 50 ml dichloromethane each time. Wash the combined organic extracts with satd. sodium chloride solution, dry over sodium sulphate, filter and concentrate by vacuum evaporation. Mix the raw product with methanol, filter, and purify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile). 0.60 g (50% of theor.) of the desired product is obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionExtract three times with 50 ml dichloromethane each time
  3. washWash the combined organic extracts with satd
  4. dry with materialsodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation
  7. additionMix the raw product with methanol
  8. filtrationfilter
  9. custompurify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-1cb1ba5667cb49b49f199a0d2d8b60ad
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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