Ammonium Hydroxide → HCID 178461972, compound

HRID 986918Notes

Reaction equation

HRID 986918 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[N:3]=1.[NH4+:18].[OH-]>C1COCC1>[Cl:8][C:6]1([NH2:18])[N:7]=[CH:2][N:3]=[C:4]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[NH:5]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 15616556HCID 15616556, compound

Product 1

HCID 178461972HCID 178461972, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-Dichloro-N2-[(1S)-1-phenylethyl]-1,3,5-triazine-2-amine, (Compound of Example 14), in THF (500 mL) was added conc. NH4OH (50 mL). The reaction mixture was stirred at ambient temperature for 48 h then was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (500 mL) and was washed with H2O (2×250 mL). The organic layer was filtered through a cotton plug then dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4-Chloro-N2-[(1S)-1-phenylethyl]-1,3,5-triazine-2,4-diamine as a white solid (29.7 g, 90%) MP 163-164° C., 1H (CDCl3) δ 7.78 (m, 5H), 6.1-6.2 (m, 4H), 1.52 (d, 3H), MS (ESI+) (M+) 249.7 obs.

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (500 mL)
  3. washwas washed with H2O (2×250 mL)
  4. filtrationThe organic layer was filtered through a cotton plug
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8018964311b46d69c7b4c059e2600ae
Source dataset
uspto-grants-2003_10
Patent number
US06630469B2

Reaction notes

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