Sodium Chloride → 4-((1R,2R)-2-benzyloxy-1-methylpropoxy)-2-chloro-5-iodopyrimidine

HRID 2199513Notes

Reaction equation

HRID 2199513 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:13])[C@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([I:24])=[CH:19][N:18]=1.[Cl-].[Na+]>C(OCC)C>[CH2:1]([O:8][C@H:9]([CH3:13])[C@@H:10]([CH3:11])[O:12][C:19]1[C:20]([I:24])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 12695195(2R,3R)-3-(Benzyloxy)butan-2-OL

Product 1

HCID 584679604-((1R,2R)-2-benzyloxy-1-methylpropoxy)-2-chloro-5-iodopyrimidineYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2R,3R)-3-Benzyloxybutan-2-ol in diethyl ether were admixed with sodium hydride in portions at 0° C. with stirring. After 10 minutes, the ice bath was removed and the mixture was stirred for a further 3 minutes at room temperature. The suspension formed was added, at 0° C., to a solution of 2,4-dichloro-5-iodopyrimidine. The mixture was stirred for 4 hours at 40° C. and then admixed with dilute sodium chloride solution. The mixture was extracted with acetic ester (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified by means of chromatography (hexane/acetic ester 4:1) (yield: 41%).

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred for a further 3 minutes at room temperature
  3. customThe suspension formed
  4. stirringThe mixture was stirred for 4 hours at 40° C.
  5. extractionThe mixture was extracted with acetic ester (2×)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe resulting residue was purified by means of chromatography (hexane/acetic ester 4:1) (yield: 41%)

Sources & evidence

ORD record
ord-ef721c7873dc4d1da370c157e9040ec5
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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