N-(3,4-dimethoxybenzyl)-7-(2-fluorobenzyl)4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine → 7-(2-fluorobenzyl)-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine

HRID 11754

Reaction equation

HRID 11754 reaction equation
COC1C=C(C=CC=1OC)C[NH:7][C:8]1[N:9]=[C:10]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)[C:11]2[CH:16]=[CH:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:12]=2[N:13]=1>C(O)(C(F)(F)F)=O>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:14]1[C:12]2[N:13]=[C:8]([NH2:7])[N:9]=[C:10]([C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[C:11]=2[CH:16]=[CH:15]1

Participants

3

Reactant 1

HCID 21976416N-(3,4-dimethoxybenzyl)-7-(2-fluorobenzyl)4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine

Product 1

HCID 99046887-(2-fluorobenzyl)-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amineYield 51.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(3,4-dimethoxybenzyl)-7-(2-fluorobenzyl)4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine (110 mg, 0.24 mmol) in TFA (1 mL) was heated to 50° C. for 3 h, concentrated in vacuo, treated with saturated NaHCO3, extracted with EtOAc, dried (MgSO4), concentrated in vacuo, purified by chromatography (EtOAc:Heptane, 1:4) and recrystallised (EtOAc) to give the title compound (38 mg, 51%) as a cream solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (EtOAc:Heptane, 1:4)
  7. customrecrystallised (EtOAc)

Sources & evidence

ORD record
ord-33bf0de3f8aa48d1816747caea2ecde9
Source dataset
uspto-grants-2006_08
Patent number
US07098333B2

Linked notes

Loading…