Formaldehyde → HCID 44250367, compound

HRID 1044657Notes

Reaction equation

HRID 1044657 reaction equation
N[C:2]1[C:3]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:4][C:5]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH2:32]=O.[C:34]([BH3-])#[N:35].[Na+].[OH-].[Na+]>C(#N)C.C(O)(=O)C>[CH3:32][N:35]([CH3:34])[C:2]1[C:3]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:4][C:5]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 442508375-Amino-2-(4-phenylpiperazin-1-yl)-4,6-dimorpholinopyrimidine

Product 1

HCID 44250367HCID 44250367, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. To a solution of 5-amino-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (425 mg, 1.0 mmol) in acetonitrile (10 ml), formalin (0.8 ml, 10 mmol), sodium cyanotrihydridoborate (188 mg, 3.0 mmol), and acetic acid (0.1 ml) was added and this was agitated for 1 hour. 2N NaOH solution was added, and extraction was carried out 2 times with dichloromethane. After washing the organic layer with saturated saline, drying was done with MgSO4, and the solvent was distilled away under reduced pressure. Purification was done by silica gel chromatography (hexane:ethyl acetate=2:1), and 260 mg of 5-dimethylamino-4,6-dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (yield 57%) was obtained. The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 141 are shown below.

Workup

  1. customThe synthesis method
  2. extractionextraction
  3. washAfter washing the organic layer with saturated saline
  4. customdrying
  5. distillationthe solvent was distilled away under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-167bf145d5d1401e91df3e7085d416fb
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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