Hydrochloric Acid → HCID 68548926, compound

HRID 1510824Notes

Reaction equation

HRID 1510824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16](O)=[O:17])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14]/[CH:15]=[CH:16]/[OH:17])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59757322HCID 59757322, compound

Product 1

HCID 68548926HCID 68548926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold mixture of 3-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl]-(2E)-acrylic acid (5 ml) in THF (50 ml) methylchloroformate (1.5 ml) was added dropwise at 0-5° C. Reaction mixture was stirred at this temperature for 30 min and sodium borohydride (0.5 g) was added at 0-5° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 30 h. After completion of the reaction, mixture was poured on a cold HCl (100 ml) and extracted with ethyl acetate (50 ml). Organic phase was washed with aqueous sodium bicarbonate (2×50 ml), dried and evaporated to give crude product which was purified by column chromatography using ethyl acetate and hexanes (1:9) to give pure 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(2E)-propenol.

Workup

  1. additionwas added dropwise at 0-5° C
  2. customReaction mixture
  3. stirringstirred at room temperature for 30 h
  4. customAfter completion of the reaction, mixture
  5. extractionextracted with ethyl acetate (50 ml)
  6. washOrganic phase was washed with aqueous sodium bicarbonate (2×50 ml)
  7. customdried
  8. customevaporated
  9. customto give crude product which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6a71473ffdae4e328c704ae19356a811
Source dataset
uspto-grants-2012_07
Patent number
US08212034B2

Reaction notes

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