Formaldehyde → HCID 67389135, compound

HRID 905695Notes

Reaction equation

HRID 905695 reaction equation
[ClH:1].Cl.NC[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[C:15]([C:26]([NH2:28])=[O:27])=[CH:14][N:13]=2)=[CH:7][CH:6]=1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.C(OCC)(=O)C.[CH3:52][N:53]([CH:55]=O)[CH3:54]>CO.C(OCC)(=O)C.O.C(N(CC)CC)C>[ClH:1].[ClH:1].[CH3:54][N:53]([CH2:55][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[C:15]([C:26]([NH2:28])=[O:27])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)[CH3:52]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 5049666Sodium triacetoxyborohydrideHCID 21866389Hydrogen chloride-ethyl acetateHCID 67388260HCID 67388260, compound

Product 1

HCID 67389135HCID 67389135, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A 7 ml portion of DMF solution containing 685 mg of 2-{[4-(aminomethyl)phenyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide dihydrochloride was mixed with 0.45 ml of triethylamine, 420 mg of 35% aqueous formalin and 1.09 g of sodium triacetoxy borohydride, followed by stirring overnight at room temperature. The reaction mixture was mixed with water, concentrated and then purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia) to obtain crude crystals. This was dissolved in a methanol-ethyl acetate mixed solution and mixed with 1 ml of 4 M hydrogen chloride/ethyl acetate solution, and the thus precipitated crystals were collected by filtration and further recrystallized (methanol-water) to obtain 164 mg of 2-({4-[(dimethylamino)methyl]phenyl}amino)-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide dihydrochloride as colorless crystals.

Workup

  1. concentrationconcentrated
  2. custompurified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia)
  3. customto obtain crude crystals
  4. filtrationthe thus precipitated crystals were collected by filtration
  5. customfurther recrystallized (methanol-water)

Sources & evidence

ORD record
ord-ba375c454ea843a0960aa6d7ec73c257
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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