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Acetonitrile → 4,6-dichloro-N-[(2R)-2-phenylpropyl]-1,3,5-triazin-2-amine

HRID 1922023
Notes
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Reaction equation

HRID 1922023 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].CC#N.[C:13]1([C@@H:19]([CH3:22])[CH2:20][NH2:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C1COCC1.O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:21][CH2:20][C@@H:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:22])[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 1547949(R)-(+)-beta-Methylphenethylamine

Product 1

HCID 866443924,6-dichloro-N-[(2R)-2-phenylpropyl]-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of cyanuric chloride (677 mg, 3.67 mmol, 1.00 equiv) in 1:1 CH3CN:H2O (6.1 mL) at 0° C. was added a solution of (2R)-2-phenyl-1-propanamine (0.52 mL, 3.7 mmol, 1.0 equiv) in THF (1.8 mL). The reaction mixture was treated with 1 N NaOH to maintain a pH of 9-10 and stirred for 10 min at 0° C. The resulting suspension was used in the next step without workup or purification. MS (ES+): m/e 282.9 [M+H]+.

Workup

  1. temperatureto maintain a pH of 9-10
  2. customThe resulting suspension was used in the next step without workup or purification

Sources & evidence

ORD record
ord-4044e96d6fed41729f8a478318745a17
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173805B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes