2-Amino-4,6-dichloropyrimidine-5-carboxaldehyde → 1-(2-Amino-4,6-dichloropyrimidin-5-yl)ethanol

HRID 857928Notes

Reaction equation

HRID 857928 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4]([Cl:11])[N:3]=1.[CH3:12][Mg+].[Br-]>C1COCC1>[NH2:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]([CH:9]([OH:10])[CH3:12])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 865983471-(2-Amino-4,6-dichloropyrimidin-5-yl)ethanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A fine suspension of 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde (3.0 g, 15 mmol); (Seela, F.; Stecker, H. Helv. Chim. Acta 1986, 69, 1602) in THF was cooled to −78° C. A 3M solution of MeMgBr in THF (25 mL, 75 mmol, 5 equiv.) was added over 3 h, keeping the internal temperature at −78° C. The mixture was stirred for a further 0.5 h, quenched with 100 ml H2O, and neutralized with aw. HCl. Extraction (EtOAc) gave 1-(2-amino-4,6-dichloro-pyrimidin-5-yl)-ethanol as a pale yellow solid (2.5 g, 76%) which was used without further purification.

Workup

  1. customat −78° C
  2. customquenched with 100 ml H2O
  3. extractionExtraction (EtOAc)

Sources & evidence

ORD record
ord-bff78fd3972343b3b29c3d11cb2bf6ad
Source dataset
uspto-grants-2006_12
Patent number
US07148228B2

Reaction notes

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