Hydrochloric Acid → HCID 68548926, compound

HRID 1881707Notes

Reaction equation

HRID 1881707 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16](OC)=[O:17])=[C:12]([CH:20]([CH3:22])[CH3:21])[N:11]=[C:10]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:9]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[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:20]([CH3:22])[CH3:21])[N:11]=[C:10]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 68545130HCID 68545130, compound

Product 1

HCID 68548926HCID 68548926, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl-amino)pyrimidin-5-yl]-1-propenoate (5.4 g) obtained in step I above was dissolved in toluene (30 ml) and the resulting solution was cooled to −78° C. To this solution, diisobutylaluminium hydride (20% solution in toluene, 45.2 ml) was added and the reaction mass was stirred at −70° C. for 15 min. Thereafter, reaction mass was poured into aqueous hydrochloric acid (1N, 30 ml). The organic layer was separated and washed with water (20 ml). The solvent was distilled under reduced pressure to yield pure (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-propen-1-ol.

Workup

  1. customThereafter, reaction mass
  2. customThe organic layer was separated
  3. washwashed with water (20 ml)
  4. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-64dacb196742418cad64e2bb7b3d8475
Source dataset
uspto-grants-2012_11
Patent number
US08318933B2

Reaction notes

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