Triethylamine → 1-(3-(4-Amino-2-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)-3-isopropylurea

HRID 1485494Notes

Reaction equation

HRID 1485494 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[N:13]=[C:14]([NH:18][C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[N:15]=[C:16]([NH2:17])[C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH:38]([N:41]=[C:42]=[O:43])([CH3:40])[CH3:39].C(OCC)(=O)C>O1CCCC1>[NH2:17][C:16]1[C:11]2[S:10][CH:9]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:42]([NH:41][CH:38]([CH3:40])[CH3:39])=[O:43])[CH:7]=[CH:6][CH:5]=3)[C:12]=2[N:13]=[C:14]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[N:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 61277Isopropyl isocyanateHCID 532379637-(3-aminophenyl)-N2-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-2,4-diamine

Product 1

HCID 532381961-(3-(4-Amino-2-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)-3-isopropylureaYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 7-(3-aminophenyl)-N2-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidin-2,4-diamine (20 mg, 0.047 mmol) synthesized in Example 11 was dissolved in anhydrous tetrahydrofuran (1 mL) and then triethylamine (20 μL, 0.14 mmol) and isopropyl isocyanate (5 mg, 0.057 mmol) were added. After stirring at room temperature for 4 hours, ethyl acetate (2 mL) was added and the mixture was washed with brine. After drying with MgSO4, the product was filtered and concentrated. Purification by silica gel chromatography (ethyl acetate/hexane, 1/1) yielded the target compound of Example 12 (18 mg, 75% yield).

Workup

  1. washthe mixture was washed with brine
  2. dry with materialAfter drying with MgSO4
  3. filtrationthe product was filtered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (ethyl acetate/hexane, 1/1)

Sources & evidence

ORD record
ord-27c370ef130847b7a310df68a21debcd
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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