(R)-(-)-2-Amino-1-propanol → HCID 58727619, compound

HRID 272634Notes

Reaction equation

HRID 272634 reaction equation
[NH2:1][C@H:2]([CH3:5])[CH2:3][OH:4].[Cl:6][C:7]1[N:12]=[C:11](Cl)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1>C(#N)C.C(OC(=O)C)C>[Cl:6][C:7]1[N:12]=[C:11]([NH:1][C@H:2]([CH3:5])[CH2:3][OH:4])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 58727619HCID 58727619, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 315 mg (4.2 mmol) of (R)-2-Amino-propan-1-ol in 5 ml of acetonitrile is added slowly to a suspension of 388 mg (2.0 mmol) of 2,4-dichloro-5-nitro-pyrimidine in 20 ml acetonitrile at −30° C. to −20° C. The batch is stirred for 3 hours at −30° C. to −20° C. The batch is diluted with ethylacetate and ice water. The batch is extracted with ethyl acetate (3×). The combined organic phases are washed with NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. 350 mg (1.51 mmol, corresponding to 76% of theory) of the product is obtained.

Workup

  1. extractionThe batch is extracted with ethyl acetate (3×)
  2. washThe combined organic phases are washed with NaCl solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. custom350 mg (1.51 mmol, corresponding to 76% of theory) of the product is obtained

Sources & evidence

ORD record
ord-04839a1312eb4cdeb3d47c277cd64378
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Reaction notes

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