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

HRID 2403560Notes

Reaction equation

HRID 2403560 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.C(#N)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

7

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 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

8.55 g (47.4 mmol) of (2R,3R)-3-benzyloxybutan-2-ol in 56 ml of diethyl ether were admixed at 0° C. with stirring in portions with 2.07 g of sodium hydride (55%). 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 6.52 g (23.7 mmol) of 2,4-dichloro-5-iodopyrimidine in 65 ml of acetonitrile. The mixture was stirred for 4 hours at 40° C. and then admixed with dilute sodium chloride solution. Extraction was carried out with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified chromatographically (hexane/ethyl acetate 4:1). This gave 4.12 g (9.8 mmol; yield: 41%) of the product.

Workup

  1. customwere admixed at 0° C.
  2. customthe ice bath was removed
  3. customThe suspension formed
  4. stirringThe mixture was stirred for 4 hours at 40° C.
  5. extractionExtraction
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe resulting residue was purified chromatographically (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-77e9bebb15304efda2fa2d23c5f86255
Source dataset
uspto-grants-2014_08
Patent number
US08802686B2

Reaction notes

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