Ethanolamine → Ethanol, 2-[[2-amino-5-[(4-chlorophenyl)ethynyl]-4-pyrimidinyl]amino]-

HRID 1271032Notes

Reaction equation

HRID 1271032 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:17]=CN(C(C)C)C(C)C)[N:3]=1.[CH2:26]([CH2:28][NH2:29])[OH:27]>C(O)C>[NH2:17][C:4]1[N:3]=[C:2]([NH:29][CH2:28][CH2:26][OH:27])[C:7]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 734464494-Chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

Product 1

HCID 9857143Ethanol, 2-[[2-amino-5-[(4-chlorophenyl)ethynyl]-4-pyrimidinyl]amino]-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.7 g of 4-chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneamino-pyrimidine, 20 mL ethanol and 0.6 mL ethanolamine was refluxed for 18 hours. The green solution was evaporated in vacuo and triturated with water. The insoluble yellow residue was recrystallized by dissolving in 35 mL hot methanol, concentrating to 10 mL and chilling. The pale yellow powdery precipitate was filtered and dried to yield 0.34 g of 2-amino-5-(4-chlorophenylethynyl)-4-(2-hyroxyethylamino)pyrimidine, m.p. 197–200° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe green solution was evaporated in vacuo
  3. customtriturated with water
  4. customThe insoluble yellow residue was recrystallized
  5. dissolutionby dissolving in 35 mL hot methanol
  6. concentrationconcentrating to 10 mL
  7. temperaturechilling
  8. filtrationThe pale yellow powdery precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-89b0b7b6b2dc4ca7aec700dedbfebed3
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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