Ammonium Chloride → HCID 16736110, compound

HRID 722096Notes

Reaction equation

HRID 722096 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[C:14]=1[Cl:25].[CH3:26][Al](C)C.[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:25][C:14]1[C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=1[CH2:12][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][C:9]([NH2:11])=[N:10][C:2]=2[CH3:26]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 11176568HCID 11176568, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 16736110HCID 16736110, compound

Reagents, catalysts & solvents 3

HCID 178420554HCID 178420554, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 6-chloro-9-(2-chloro-3,4,5-trimethoxy-benzyl)-9H-purin-2-ylamine, see example 97) (0.2 mmol) and tetrakis(triphenylphosphino)-palladium (0.02 mmol) in dry THF (3 mL) was treated with trimethylaluminum (2M in toluene, 0.45 mmol) under nitrogen and heated to reflux for 3 h. The reaction mixture was cooled to r.t., diluted with toluene (5 mL) and quenched with methanol (0.5 mL) followed by ammonium chloride (1 mmol). The mixture was heated to reflux for 2 h and filtered, while hot, on Celite. See J. Med. Chem. 1999, 42, 2064–2086. TLC (100% EtOAc) Rf was 0.2. HPLC Rt: 4.800 min.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customquenched with methanol (0.5 mL)
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 2 h
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c0bd738012a54a28a30480153156c942
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

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