Sodium Hydroxide → HCID 18946288, compound

HRID 1768959Notes

Reaction equation

HRID 1768959 reaction equation
C([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:21]=[CH:20][C:16]([CH2:17][C:18]#[N:19])=[CH:15][CH:14]=2)[CH2:5][CH2:4]1)=O.[N:22]([C:24]1[C:25]([NH2:32])=[N:26][C:27]([NH2:31])=[N:28][C:29]=1[NH2:30])=O.C(OCC[O-])C.[Na+].[OH-].[Na+]>C(OCCO)C.CCOCC>[N:6]1([CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]3[N:22]=[C:24]4[C:25](=[N:32][C:18]=3[NH2:19])[N:26]=[C:27]([NH2:31])[N:28]=[C:29]4[NH2:30])=[CH:20][CH:21]=2)[CH2:5][CH2:4][NH:3][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 705045-Nitroso-2,4,6-pyrimidinetriamineHCID 18946279HCID 18946279, compoundHCID 23667900Sodium 2-ethoxyethoxide

Product 1

HCID 18946288HCID 18946288, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 4-[3-(4-formyl-1-piperazinyl)propylamino]benzylcyanide (1.15 g, 4.0 mmol), 5-nitroso-2,4,6-triamino-pyrimidine (0.56 g, 3.6 mmol) and 0.2N sodium-(2-ethoxy-ethoxide) in 2-ethoxyethanol (18 ml) was stirred under reflux for 3 hours, then NaOH (0.14 g, 3.5 mmol) was added and stirring under reflux was continued for further 2.5 hours. After cooling the mixture was diluted with 100 ml of ether. The separated precipitate was collected, washed with ether, then with water and dried to afford the title compound (0.92 g) as a yellow powder, yield: 64.8%. The above product was dissolved in a hot solution of L(+)-tartaric. acid (0.75 g, 5 mmol) in water (6 ml) and after cooling the mixture was diluted with methanol (6 ml). The separated crystals were collected, washed with methanol and dried to give the ditartrate of the title compound, mp. 170°-178° C. Yield of the salt formation: 51.9%.

Workup

  1. temperatureunder reflux for 3 hours
  2. stirringstirring
  3. temperatureunder reflux
  4. temperatureAfter cooling the mixture
  5. customThe separated precipitate was collected
  6. washwashed with ether
  7. dry with materialwith water and dried

Sources & evidence

ORD record
ord-e51f0e00a8ea4bcfa3a0f152a8d646f5
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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