Formaldehyde → 2-(4-Methyl-piperazin-1-yl)-4-thiophen-3-yl-[1,3,5]triazine

HRID 910669Notes

Reaction equation

HRID 910669 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:22](C)=O.[Na+]>C(Cl)Cl.CO>[CH3:22][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[C:11]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[N:10]=[CH:9][N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 673880172-Piperazin-1-yl-4-thiophen-3-yl-[1,3,5]triazine

Product 1

HCID 576132112-(4-Methyl-piperazin-1-yl)-4-thiophen-3-yl-[1,3,5]triazine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-piperazin-1-yl-4-thiophen-3-yl-[1,3,5]triazine (0.17 mmol) in CH2Cl2/MeOH (3:1, 4 mL) was added formaldehyde (37 wt. % in water, 22 mg, 0.26 mmol). After stirring for 1 h at room temperature, NaB(OAc)3H (72.8 mg, 0.34 mmol) was added. The reaction mixture was stirred overnight at room temperature, then quenched with 1 N NaOH (3 mL), and extracted with EtOAc (50 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried, and concentrated to yield a light yellow oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customquenched with 1 N NaOH (3 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic layer was washed with water (2×15 mL), brine (15 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto yield a light yellow oil

Sources & evidence

ORD record
ord-b5cb7ca2f1214a4fa94f986f65d7bcd0
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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