Triethylamine → 2-(4-Hydroxyphenyl)-5-octylpyrimidine

HRID 2392977Notes

Reaction equation

HRID 2392977 reaction equation
O=P(Cl)(Cl)Cl.CO[CH:8](OC)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[NH:33])=[CH:30][CH:29]=1)C1C=CC=CC=1.[CH2:37](N(CC)CC)C>CN(C=O)C>[OH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]2[N:34]=[CH:8][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:37][N:33]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24513Decane, 1,1-dimethoxy-HCID 24813Phosphorus oxychlorideHCID 98374594-BENZYLOXY-BENZAMIDINE

Product 1

HCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

137.7 ml (1.5 mol) of POCl3 are added with ice cooling to 135 g (1.85 mol) of DMF, and the mixture is subsequently stirred at room temperature for 15 minutes. 202 g (1 mol) of decanal dimethyl acetal dissolved in 500 ml of DMF are then. added dropwise, and, after addition is complete, the mixture is stirred for about 3 further hours. 262.5 g (1 mol) of 4-benzoxybenzamidine are subsequently added, and the mixture is stirred for a further hour. 1.1 l of triethylamine are then slowly added, during which the temperature rises to about 70° C. In order to maintain stirrability, about 700 ml of DMF are added, and the triethylamine is subsequently removed by distillation at atmospheric pressure. The residue is poured into about 6 l of ice water. The precipitated product is washed with water, recrystallized from 2.5 1 of isobutanol, dissolved in 1 l of ethyl acetate and hydrogenated at atmospheric pressure with addition of 10 g of Pd/C (10%) until take-up of hydrogen ceases. The catalyst is filtered off with suction, and the residue from evaporation of the filtrate is dried at 50° C. under reduced pressure.

Workup

  1. additionadded dropwise
  2. additionafter addition
  3. stirringthe mixture is stirred for about 3 further hours
  4. stirringthe mixture is stirred for a further hour
  5. customrises to about 70° C
  6. additionare added
  7. customthe triethylamine is subsequently removed by distillation at atmospheric pressure
  8. additionThe residue is poured into about 6 l of ice water
  9. washThe precipitated product is washed with water
  10. customrecrystallized from 2.5 1 of isobutanol
  11. dissolutiondissolved in 1 l of ethyl acetate and hydrogenated at atmospheric pressure with addition of 10 g of Pd/C (10%)
  12. filtrationThe catalyst is filtered off with suction
  13. customthe residue from evaporation of the filtrate
  14. customis dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-4160599bf9624ac9a55f975ceded5d3e
Source dataset
uspto-grants-1998_09
Patent number
US05804097

Reaction notes

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