Ammonia → 6-Chloropyrimidine-2,4,5-triamine hydrochloride

HRID 600437Notes

Reaction equation

HRID 600437 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[C:4](Cl)[N:3]=1.N.[OH-].[Na+].FC1C=CC2N=C[N:20](C3N=C4C(NC(=O)N4C4CCOCC4)=C(C(N4CCCCC4)=O)N=3)C=2C=1>O>[ClH:8].[Cl:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH2:20])[C:5]=1[NH2:9]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 3010392,5-Diamino-4,6-dichloropyrimidineHCID 576127022-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(piperidine-1-carbonyl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

Product 1

HCID 457898366-Chloropyrimidine-2,4,5-triamine hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-chloropyrimidine-2,4,5-triamine hydrochloride was prepared as described in WO 94/07892. 2,5-Diamino-4,6-dichloropyrimidine (10.8 g, 60.3 mmol) and concentrated aqueous ammonia (30 mL) were heated together in a sealed tube at 105° C. for 18 h, then cooled to room temperature. 2.34 g NaOH in water (10 mL) was added and the excess ammonia stripped out by concentrating to a low volume. Dilute HCl 2N (35 mL) and water (10 mL) were added and heated to dissolve, cooled to crystallize, then filtered to give the desired 6-chloropyrimidine-2,4,5-triamine hydrochloride (87% yield). MS (EI) m/z 160.1 (MH)+.

Workup

  1. custom6-chloropyrimidine-2,4,5-triamine hydrochloride was prepared
  2. concentrationby concentrating to a low volume
  3. additionDilute HCl 2N (35 mL) and water (10 mL) were added
  4. temperatureheated
  5. dissolutionto dissolve
  6. temperaturecooled
  7. customto crystallize
  8. filtrationfiltered

Sources & evidence

ORD record
ord-e2d534d2156248079977aa37f6f5a7bf
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…