Triethylamine → HCID 19734388, compound

HRID 327029Notes

Reaction equation

HRID 327029 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[NH2:10][CH2:11][C:12]1[O:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>O>[NH2:8][C:7]1[C:2]([NH:10][CH2:11][C:12]2[O:16][C:15]([CH2:17][OH:18])=[CH:14][CH:13]=2)=[N:3][CH:4]=[N:5][C:6]=1[Cl:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidineHCID 448213(5-(Aminomethyl)furan-2-yl)methanol

Product 1

HCID 19734388HCID 19734388, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.3 parts of 4,6-dichloro-5-pyrimidinamine, 14 parts of 5-(aminomethyl)-2-furanmethanol, 12 parts of N,N-diethylethanamine and 200 parts of water was stirred for 10 hours at reflux temperature. The reaction mixture was evaporated and the residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH(NH3) 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 19.5 parts (76.6%) of 5-[[(5-amino-6-chloro-4-pyrimidinyl)amino]methyl]-2-furanmethanol; mp. 136.7° C. (interm. 17).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH(NH3) 95:5)
  4. customThe eluent of the desired fraction was evaporated
  5. customthe residue was crystallized from acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-a4d7ede076264065ab31026220d6d670
Source dataset
uspto-grants-1993_12
Patent number
US05272150

Reaction notes

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