4,6-Dichloropyrimidine → (S)-6-chloro-N-(1-phenylethyl)pyrimidin-4-amine

HRID 986916Notes

Reaction equation

HRID 986916 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC#N>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:17][C@H:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 758181-Phenethylamine, (-)-

Product 1

HCID 59099930(S)-6-chloro-N-(1-phenylethyl)pyrimidin-4-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,6-dichloropyrimidine (14.9 g, 100 mmole) and (1S)-1-phenylethylamine (13.3 g, 110 mmole) in CH3CN (100 mL) was refluxed for 4 hours. The reaction was partitioned between Et2O (500 mL) and H2O (250 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel 60 with Hexane/EtOAc 3:1. Pure fractions were combined, concentrated under reduced pressure, and dried under high vacuum to afford the titled compound (18.6 g, 80%) as a yellow oil. 1H NMR (CDCl3): δ 1.57 (d, J=7.0 Hz, 3H), 4.6 (b s,1H), 5.6 (b s,1H), 6.19 (s,1H), 7.34 (m, 5H), 8.30 (s,1H); LC/MS (MH+) 233.62.

Workup

  1. customThe reaction was partitioned between Et2O (500 mL) and H2O (250 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel 60 with Hexane/EtOAc 3:1
  6. concentrationconcentrated under reduced pressure
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-673b3d29a86f4b16a22c76fc216553ad
Source dataset
uspto-grants-2003_10
Patent number
US06630469B2

Reaction notes

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