1-Hydroxybenzotriazole → 2-Amino-4-[1-(3,4-dihydroxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidine

HRID 617187Notes

Reaction equation

HRID 617187 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:3]=1.C([O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[O:40]CC1C=CC=CC=1)[C:34](O)=[O:35])C1C=CC=CC=1.ON1C2C=CC=CC=2N=N1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([CH:17]2[CH2:22][CH2:21][N:20]([C:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:39]([OH:40])=[C:31]([OH:30])[CH:32]=3)[CH2:19][CH2:18]2)[CH:5]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[N:7]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 108541553,4-Bis(benzyloxy)benzoic acidHCID 218515322-Amino-4-(4-methoxyphenylmethyl)-6-(4-piperidinyl)pyrimidine

Product 1

HCID 218515152-Amino-4-[1-(3,4-dihydroxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl)pyrimidineYield 203.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-(4-methoxyphenylmethyl)-6-(4-piperidinyl)pyrimidine (160 mg, 0.54 mmol), 3,4-dibenzyloxybenzoic acid (179 mg, 0.54 mmol) and 1-hydroxybenzotriazole (72 mg, 0.54 mmol) in dichioromethane (150 ml) were added 1-ethyl-3-(N, N'-dimethylaminopropyl)carbodiimide hydrochloride (103 mg, 0.54 mmol) at room temperature under nitrogen atmosphere. After stirring for about 30 minutes, the mixture was washed successively with saturated sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate and then evaporated. The residue was purified by column chromatography (chloroform:methanol=99:1) to give the titled compound (477 mg).

Workup

  1. washthe mixture was washed successively with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography (chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-e62d668a608c4f56a3b66dc3b0649675
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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