Sodium triacetoxyborohydride → HCID 59588026, compound

HRID 40753Notes

Reaction equation

HRID 40753 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:11]=[C:10]([F:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:23]([CH3:25])=O.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([F:20])[CH:11]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:23][CH3:25])[CH2:16][CH2:15]3)[CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 595882342-Cloro-4-(3-fluoro-5-(piperazin-1-yl)phenyl)pyrimidine

Product 1

HCID 59588026HCID 59588026, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Cloro-4-(3-fluoro-5-(piperazin-1-yl)phenyl)pyrimidine (0.29 g, 1 mmol) and ethyl aldehyde (0.13 g, 3 mmol) were mixed in dichloroethane (10 mL) and then added with NaBH(OAc)3 (0.64 g, 3 mmol). After stirring at room temperature under argon for overnight, the reaction mixture was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was separated, dried with anhydrous MgSO4 and concentrated in vacuo to give desired product 2-Chloro-4-(3-(4-ethylpiperazin-1-yl)-5-fluorophenyl)pyrimidine.

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5dbf0ff77be47798991b4edd04599db
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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