Triethylamine → HCID 59674059, compound

HRID 1891070Notes

Reaction equation

HRID 1891070 reaction equation
Cl.[NH2:2][C@H:3]([CH2:7][O:8][CH3:9])[C@H:4]([OH:6])[CH3:5].C(N(CC)CC)C.[Br:17][C:18]1[C:19](Cl)=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1>C(#N)C>[Br:17][C:18]1[C:19]([NH:2][C@H:3]([CH2:7][O:8][CH3:9])[C@H:4]([OH:6])[CH3:5])=[N:20][C:21]([Cl:24])=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 86600126HCID 86600126, compound

Product 1

HCID 59674059HCID 59674059, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

311 mg (2.6 mmol) of (2R,3R)-3-amino-4-methoxy-butan-2-ol hydrochloride (production according to A. I. Meyers, D. Hoyer, Tet. Lett. 1985, 26, 4687) in 2 ml of acetonitrile is mixed with 0.28 ml of triethylamine and shaken. It is filtered, and the filter cakes are washed with 2 ml of acetonitrile. The filtrate is added in drops to a solution of 455 mg (2.0 mmol) of 5-bromo-2,4dichloro-pyrimidine in 26 ml of acetonitrile at −30° C. By removal of the cooling bath, it is slowly heated to room temperature while being stirred. After 16 hours, the solvent is drawn off in a rotary evaporator, and the remaining residue is purified by chromatography (hexane/ethyl acetate: 4:1-1:1). 509 mg (1.6 mmol, corresponding to 80% of theory) of the product is obtained.

Workup

  1. filtrationIt is filtered
  2. washthe filter cakes are washed with 2 ml of acetonitrile
  3. customBy removal of the cooling bath, it
  4. stirringwhile being stirred
  5. customthe solvent is drawn off in a rotary evaporator
  6. customthe remaining residue is purified by chromatography (hexane/ethyl acetate: 4:1-1:1)
  7. custom509 mg (1.6 mmol, corresponding to 80% of theory) of the product is obtained

Sources & evidence

ORD record
ord-f2ab68db231843c69d6a1afd9503e40b
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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