Sodium borohydride → HCID 57636081, compound

HRID 216107Notes

Reaction equation

HRID 216107 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH:6]=[C:5]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:4]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][CH:16]=2)[CH:6]=[C:5]([NH:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[N:4]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57636122HCID 57636122, compound

Product 1

HCID 57636081HCID 57636081, compoundYield 109.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde [33 mg, 0.08 mmol, Example 35(u)] in a mixture of DCM (3 mL) and MeOH (1 mL) is treated with sodium borohydride (100 mg). After 10 minutes at 20° C., the mixture is concentrated, and extracted twice with EtOAc (10 mL). The combined extracts are dried over magnesium sulfate and filtered through a plug of silica gel to afford (3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-methanol [32 mg, 100%, Example 9(c)]. LCMS: RT=2.18 minutes, MS: 366 (M+H).

Workup

  1. concentrationthe mixture is concentrated
  2. extractionextracted twice with EtOAc (10 mL)
  3. dry with materialThe combined extracts are dried over magnesium sulfate
  4. filtrationfiltered through a plug of silica gel

Sources & evidence

ORD record
ord-1e1d3fbf8ce6430484e1e0bf39176a54
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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