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Ammonium Chloride → N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1630335
Notes
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Reaction equation

HRID 1630335 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[N:16]=[C:15]([NH:17][CH3:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:13][N:12]=1)[C:5]#[N:6].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:23]=[N:24][NH:25][N:6]=2)[CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[N:16]=[C:15]([NH:17][CH3:18])[C:14]([C:19]([F:20])([F:21])[F:22])=[CH:13][N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 715133123-Chloro-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzonitrile

Product 1

HCID 71513313N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamineYield 85%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
125 °C

Procedure

To a solution of 3-chloro-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzonitrile (135 mg, 6.41 mmol) in DMF (2 mL) was added sodium azide (80 mg, 1.24 mmol) and ammonium chloride (66 mg, 1.24 mmol). The mixture was heated at 125° C. for 18 h. The mixture was cooled, filtered and the solid washed with ethyl acetate. The filtrated was concentrated under reduced pressure and the crude residue was diluted with water (5 mL) and diethyl ether (5 mL). A precipitate formed which was filtered and washed with further portions of water and diethyl ether. The solid was co-evaporated with dichloromethane and methanol and then dried in a vacuum oven to yield N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (130 mg, 85%). LCMS (ESCI_Formic_MeCN): [MH+]=371 at 3.11 min. 1H NMR (400 MHz, DMSO): δ 8.94 (s, 1H); 8.26-8.19 (m, 2H); 8.14 (d, J=2.0, 1H); 8.03-7.96 (m, 1H); 7.30-7.22 (m, 1H); 2.89 (t, J=4.4, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe solid washed with ethyl acetate
  4. concentrationThe filtrated was concentrated under reduced pressure
  5. additionthe crude residue was diluted with water (5 mL) and diethyl ether (5 mL)
  6. customA precipitate formed which
  7. filtrationwas filtered
  8. washwashed with further portions of water and diethyl ether
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4d72974d461d48748cf9e0457109dcc8
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes