Ammonium Chloride → HCID 18763636, compound

HRID 431251Notes

Reaction equation

HRID 431251 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[N:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[N:5]=[C:4](/[CH:13]=[CH:14]/[C:15]2[CH:22]=[CH:21][CH:20]=[C:17]([C:18]3[N:23]=[N:24][NH:25][N:19]=3)[CH:16]=2)[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 9947955HCID 9947955, compound

Product 1

HCID 18763636HCID 18763636, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 100 mg (0.34 mmol) of (E)-3-[2-(4-methyl-6-pyrrolidin-1-yl-pyrimidin-2-yl)-vinyl]-benzonitrile, 448 mg (6.9 mmol) NaN3 and 368 mg (6.9 mmol) NH4Cl in 10 ml DMF was heated at 70° C. for 20 h until completion of the reaction according to TLC analysis. The reaction mixture was cooled to RT, concentrated in vacuo and then partitioned between 1N HCl and CH2Cl2. The organic layer was separated and the aqueous layer extracted several times with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crystalline solid which formed was filted off by suction and dried in a high vacuum to give ((E)-4-methyl-6-pyrrolidin-1-yl-2-{2-[3-(2H-tetrazol-5-yl)-phenyl]-vinyl}-pyrimidine (20 mg, 17.4%) as an off-white solid. ISP mass spectrum, m/e: 334.3 (M+1 calculated for C18H19N7: 334).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. custompartitioned between 1N HCl and CH2Cl2
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted several times with CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crystalline solid which formed
  9. customdried in a high vacuum

Sources & evidence

ORD record
ord-2cc6707f2efc4964ba744687215f85b4
Source dataset
uspto-grants-2003_12
Patent number
US06657060B2

Reaction notes

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