5-Nitroso-2,4,6-pyrimidinetriamine → HCID 18946285, compound

HRID 1768950Notes

Reaction equation

HRID 1768950 reaction equation
[Na].[N:2]([C:4]1[C:5]([NH2:12])=[N:6][C:7]([NH2:11])=[N:8][C:9]=1[NH2:10])=O.[OH:13][CH:14]([CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1)[CH2:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([CH2:21][C:22]#[N:23])=[CH:19][CH:18]=1>C(OCCO)C>[OH:13][CH:14]([CH2:26][N:27]1[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]1)[CH2:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]2[N:2]=[C:4]3[C:5](=[N:12][C:22]=2[NH2:23])[N:6]=[C:7]([NH2:11])[N:8]=[C:9]3[NH2:10])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 705045-Nitroso-2,4,6-pyrimidinetriamineHCID 5360545SodiumHCID 18946292HCID 18946292, compound

Product 1

HCID 18946285HCID 18946285, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Sodium metall (0.22 g, 9.6 mg-atom) was dissolved in 2-ethoxyethanol (60 ml) at 40°-50° C., the solution was cooled to room temperature and 5-nitroso-2,4,6-triamino-pirimidine (1.46 g, 9.5 mmol) was added, followed by 4-[2-hydroxy-3-[4-(tert-butoxy-carbonyl)-1-piperazinyl]propoxy]benzylcyanide (3.92 g, 10.4 mmol) prepared as described in Example 45. The mixture was stirred under reflux in an atmosphere of nitrogen for one hour and the obtained dark brown solution was cooled to room temperature. After dilution with 200 ml of ethyl acetate the precipitate was collected, washed with ethyl acetate and dried to yield a yellow powder, mp. 244°-246° C. (dec.). The filtrate was concentrated and the residue was dissolved in 30 ml of methanol. After treatment with decolorizing carbon the solution was concentrated to a volume of 10 ml and the separated crystals were collected. Total yield of the two generations: 84.8%.

Workup

  1. customprepared
  2. temperatureunder reflux in an atmosphere of nitrogen for one hour
  3. temperaturethe obtained dark brown solution was cooled to room temperature
  4. customAfter dilution with 200 ml of ethyl acetate the precipitate was collected
  5. washwashed with ethyl acetate
  6. customdried
  7. customto yield a yellow powder, mp. 244°-246° C. (dec.)
  8. concentrationThe filtrate was concentrated
  9. dissolutionthe residue was dissolved in 30 ml of methanol
  10. concentrationAfter treatment with decolorizing carbon the solution was concentrated to a volume of 10 ml
  11. customthe separated crystals were collected

Sources & evidence

ORD record
ord-1d7db4784b0b433dacee0be63a3a2af8
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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