Diglycolamine → 2-Amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynyl pyrimidine

HRID 1271036Notes

Reaction equation

HRID 1271036 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:16]=CN(C(C)C)C(C)C)[N:3]=1.[NH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31]>C(O)C>[NH2:16][C:4]1[N:3]=[C:2]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])[C:7]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 734464524-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

Product 1

HCID 98574242-Amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynyl pyrimidineYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.5 g of 4-chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine, 20 mL of ethanol and 1.83 g of 2-(2-aminoethoxy)ethanol was refluxed for 18 hours. The tea colored solution was evaporated in vacuo and the residue partitioned between water and dichloromethane. The aqueous layer was washed twice more with dichloromethane and the combined organic extracts washed with water. The organic solution was dried over sodium sulfate, filtered and evaporated in vacuo. The yellow residue obtained was triturated with ether and filtered to give 0.49 g of a yellow solid, 2-amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynylpyrimidine. m.p. 128–129° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe tea colored solution was evaporated in vacuo
  3. customthe residue partitioned between water and dichloromethane
  4. washThe aqueous layer was washed twice more with dichloromethane
  5. washthe combined organic extracts washed with water
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe yellow residue obtained
  10. customwas triturated with ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-fb1d7b06e0004458b46d0c6a48157306
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

Loading…