HCID 18916654, compound → HCID 18916868, compound

HRID 1290668Notes

Reaction equation

HRID 1290668 reaction equation
[CH3:1][N:2]([CH3:44])[C:3]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([NH2:23])=[C:11]([O:24][C:25]2[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:26]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:10]=1)=[O:4].[CH2:45]1COC[CH2:46]1.C(O)C>>[CH3:1][N:2]([CH3:44])[C:3]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[O:8][C:9]1[N:14]=[C:13]2[C:12]([N:23]=[C:45]([CH3:46])[N:15]2[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:11]([O:24][C:25]2[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:26]=2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:10]=1)=[O:4]

Participants

3

Reactant 2

HCID 18916654HCID 18916654, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 18916868HCID 18916868, compound

Conditions

Temperature
170 °C

Procedure

2-(3-Dimethylaminocarbonylphenoxy)-4-(benzyl)amino-5-amino-6-(2-benzyloxy-5-cyanophenoxy)pyrimidine, a compound of formula (J), (0.26 g, 0.44 mmol), was treated with ethyl imidate hydrochloride (0.17 g, 1.3 mmol) in THF/ethanol at 80° C for 6 hours and then concentrated to an oil. The residue was heated in a sand bath under vacuum at 170° C. for 2.0 hours, cooled and filtered through a pad of silica, eluting with 5% methanol in methylene chloride. Evaporation of the volatiles afforded 0.20 g of 2-(3-dimethylaminocarbonylphenoxy)-6-(2-benzyloxy-5-cyanophenoxy)-8-methyl-9-benzylpurine, a compound of formula (L).

Workup

  1. concentrationconcentrated to an oil
  2. temperaturecooled
  3. filtrationfiltered through a pad of silica
  4. washeluting with 5% methanol in methylene chloride
  5. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-3c3ff095ef0a47169563223321ac2f26
Source dataset
uspto-grants-1998_05
Patent number
US05753635

Reaction notes

Loading…