Ethylene Glycol → HCID 135621416, compound

HRID 1085075Notes

Reaction equation

HRID 1085075 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].[CH2:9]([OH:12])[CH2:10]O.[C:13]([OH:16])(=O)[CH3:14].[OH-].[NH4+:18]>O>[OH:16][CH2:13][CH2:14][C:10]1[C:9](=[O:12])[NH:18][C:6]([NH:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:1][C:2]=1[CH3:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 195092-Pyridinemethanamine

Product 1

HCID 135621416HCID 135621416, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 20 parts of 2-pyridinemethanamine, 37 parts of intermediate 1,200 parts of 1,2-ethanediol and 1.05 parts of acetic acid was stirred for 4 hours at 160° C. After cooling, the mixture was stirred in water, which was slightly basified with ammonium hydroxide. The whole was extracted with trichloromethane. The aqueous layer was evaporated and the residual oil was stirred with some 2-propanol for 1 hour. The product was filtered off, washed with 2-propanol and dried, yielding 21 parts (44.1%) of 5-(2-hydroxyethyl)-6-methyl-2-[(2-pyridinylmethyl)amino]-4(3H)-pyrimidinone; mp.-185° C. (interm. 21).

Workup

  1. temperatureAfter cooling
  2. extractionThe whole was extracted with trichloromethane
  3. customThe aqueous layer was evaporated
  4. stirringthe residual oil was stirred with some 2-propanol for 1 hour
  5. filtrationThe product was filtered off
  6. washwashed with 2-propanol
  7. customdried

Sources & evidence

ORD record
ord-0a3bcb8ea4c24ea59420179b64e3d05a
Source dataset
uspto-grants-1991_04
Patent number
US05008268

Reaction notes

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