1-Butanol → Ethyl 4-((2-chloro-9-(tetrahydro-3-thienyl)-9H-purin-6-yl)-amino)-benzoate

HRID 1272635Notes

Reaction equation

HRID 1272635 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][S:13][CH2:12]2)=[C:4](Cl)[N:3]=1.C(O)CCC.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][S:13][CH2:12]2)=[C:4]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:32][CH:33]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 2337BenzocaineHCID 219229912,6-dichloro-9-(tetrahydro-3-thienyl)-9H-purine

Product 1

HCID 21923000Ethyl 4-((2-chloro-9-(tetrahydro-3-thienyl)-9H-purin-6-yl)-amino)-benzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The operation is carried out as in Stage 2 of Example 5 starting from 160 mg of the product obtained in Stage 1 of Example 5, 3 ml of butanol and using 100 mg of ethyl 4-aminobenzoate in place of the benzylamine and the reaction medium is taken to a temperature of approximately 80 to 85° C. for 30 hours, left to return to ambient temperature, diluted with 3 ml of isopropanol, placed for approximately one hour at a temperature of approximately 0° C., followed by separating, washing with 5 ml of isopropanol and drying under vacuum at a temperature of approximately 50° C. After purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10, 202 mg of expected product is thus obtained in the form of white-cream crystals.

Workup

  1. waitleft
  2. customto return to ambient temperature
  3. waitplaced for approximately one hour at a temperature of approximately 0° C.
  4. customby separating
  5. washwashing with 5 ml of isopropanol
  6. customdrying under vacuum at a temperature of approximately 50° C
  7. customAfter purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10, 202 mg of expected product
  8. customis thus obtained in the form of white-cream crystals

Sources & evidence

ORD record
ord-17e15c27b19d483db6c5c20b2687c2e3
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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