Sodium cyanoborohydride → 5-[3-(Indan-2-yloxy)-4-Methoxyphenyl]-1,2,3,4-Tetrahydro-2-Pyrimidinone

HRID 36474Notes

Reaction equation

HRID 36474 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C:19]2[CH:20]=[N:21][C:22](=[O:25])[NH:23][CH:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[BH3-]C#N.[Na+]>C(O)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[CH:12]=[C:13]([C:19]2[CH2:24][NH:23][C:22](=[O:25])[NH:21][CH:20]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 193788965-[3-(Indan-2-yloxy)-4-methoxyphenyl]-1,2-dihydro-2-pyrimidinone

Product 1

HCID 140102015-[3-(Indan-2-yloxy)-4-Methoxyphenyl]-1,2,3,4-Tetrahydro-2-PyrimidinoneYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-[3-(Indan-2-yloxy)-4-methoxyphenyl]-1,2-dihydro-2-pyrimidinone (740 mg, 2.2 mmol) is dissolved in 10 ml. acetic acid cooled in an ice bath and treated with NaCNBH3 (140 mg, 2.2 mmol). The reaction is stirred for hours and is worked up by dilution with water and extraction with ethyl acetate. The collected organics are washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 640 mg (87.4%) of the title product as a white crystalline solid.

Workup

  1. extractionis worked up by dilution with water and extraction with ethyl acetate
  2. washThe collected organics are washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be8bb39d61454ae0a47f5dd1119bd4ad
Source dataset
uspto-grants-1995_05
Patent number
US05414127

Reaction notes

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