Formaldehyde → HCID 16119481, compound

HRID 2053089Notes

Reaction equation

HRID 2053089 reaction equation
F[C:2](F)(F)C(O)=O.[N:8]1([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[N:18]=[C:17]([C:31]#[N:32])[N:16]=2)[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:2][N:11]1[CH2:12][CH2:13][CH2:14][N:8]([C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)[N:18]=[C:17]([C:31]#[N:32])[N:16]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86612501HCID 86612501, compound

Product 1

HCID 16119481HCID 16119481, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[1,4]Diazepan-1-yl-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (Example 13; 30 mg) and formaldehyde (6 mg, 37% wt aqueous) were stirred at room temperature in methanol (500 μl) for ten minutes. Sodium triacetoxyborohydride (17 mg) was added to the reaction and stirring continued for two hours. Solvent was evaporated under reduced pressure to yield crude product. Purification by flash chromatography on silica yielded product 4-(4-methyl-[1,4]diazepan-1-yl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (10 mg).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customto yield crude product
  3. customPurification by flash chromatography on silica yielded product 4-(4-methyl-[1,4]diazepan-1-yl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (10 mg)

Sources & evidence

ORD record
ord-ac206327d3dc47c08c88906417418afe
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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