Dimethylformamide → HCID 67620079, compound

HRID 2294021Notes

Reaction equation

HRID 2294021 reaction equation
Cl[CH2:2][C:3]1[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1.C([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.[CH2:18]([O:25][CH2:26]C1CCNCC=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:33]N(C)C=O>>[CH2:18]([O:25][C:26]1[CH2:17][CH2:16][N:13]([CH:2]([CH3:33])[C:3]2[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=2)[CH2:14][CH:15]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidineHCID 21473631HCID 21473631, compound

Product 1

HCID 67620079HCID 67620079, compoundYield 53%

Procedure

A suspension of 0.327 g (0.001 68 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 8 ml of dimethylformamide was treated with 0.7 ml (0.0050 mol) of triethylamine and 0.37 g (0.00168 mol) of 4-benzyloxymethyl-1,2,3,6-tetrahydro-pyridine (contaminated with 30% of 1-benzyl-4-benzyloxymethyl-1,2,3,6-tetrahydro-pyridine) and the mixture was stirred at room temperature under argon for 18 hours. The solvent was distilled off in a high vacuum. The residue was partitioned between dichloromethane/water, extracted and dried over MgSO4. After removing the solvent the residue was chromatographed on silica gel with ethyl acetate as the eluent. 0.19 g (53%) of [5-(4-benzyloxy-methyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-2-methyl-pyrimidin-4-yl]-amine was obtained as a yellow oil. MS (ISP): me/e=325 (C19 H25N4O+).

Workup

  1. distillationThe solvent was distilled off in a high vacuum
  2. customThe residue was partitioned between dichloromethane/water
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-607d9f1debe9435ab7e910e3eb537cc4
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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