Dimethylformamide dimethyl acetal → HCID 488740, compound

HRID 2305419Notes

Reaction equation

HRID 2305419 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[NH2:9][C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[N:13]=[C:12]([NH:25][C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[N:11]=1>>[C:30]([C:29]1[CH:32]=[CH:33][C:26]([NH:25][C:12]2[N:11]=[C:10]([N:9]=[CH:3][N:4]([CH3:6])[CH3:5])[CH:15]=[C:14]([CH2:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[N:13]=2)=[CH:27][CH:28]=1)#[N:31]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 486363HCID 486363, compound

Product 1

HCID 488740HCID 488740, compoundYield 44.1%

Procedure

1,1-Dimethoxy-N,N-dimethylmethanamine (0.152 mol) was added to 4-[[4-amino-6-[(2,6-dichlorophenyl)methyl]-2-pyrimidinyl]amino]benzonitrile (0.0008 mol). The mixture was stirred at room temperature for 2 days and then concentrated. The crude product was purified by flash chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1). The desired fraction was collected and the solvent was evaporated. The resulting residue was triturated with hexane, yielding 0.15 g (42%) of N′-[2-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-4-pyrimidinyl]-N,N-dimethylmethanimidamide (comp. 26; mp. 175-180° C.).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by flash chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1)
  3. customThe desired fraction was collected
  4. customthe solvent was evaporated
  5. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-a69a41854ada42099aef83dc8884d066
Source dataset
uspto-grants-2002_08
Patent number
US06440986B2

Reaction notes

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