Ethyl Acetate → HCID 67360035, compound

HRID 1464986Notes

Reaction equation

HRID 1464986 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[C:5]=2[N:6]=[CH:7][N:8]=1.CN(C(ON1N=N[C:25]2[CH:26]=[CH:27][CH:28]=[N:29][C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:39][CH2:40]N(C(C)C)C(C)C.[C:48]([O:51][CH2:52][CH3:53])(=[O:50])C>CN(C=O)C>[CH3:39][C:40]1[CH:24]=[CH:25][C:26]([C:48]([O:51][CH2:52][CH3:53])=[O:50])=[CH:27][C:28]=1[NH:29][C:12]([C:9]1[C:5]2[N:6]=[CH:7][N:8]=[C:3]([S:2][CH3:1])[C:4]=2[S:11][CH:10]=1)=[O:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67328452HCID 67328452, compound

Product 1

HCID 67360035HCID 67360035, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

4-(Methylthio)thieno[3,2-d]pyrimidine-7-carboxylic acid (2 g, 10.2 mmol) obtained in Step 3 of Preparation Example 2 was dissolved in DMF (40 mL), methyl 3-amino-4-methyl benzoate (1.2 g, 7.3 mmol), HATU (8.3 g, 22 mmol) and DIPEA (6.4 mL, 36.6 mmol) were added thereto and stirred at 45° C. for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with an aqueous sodium bicarbonate solution and brine, sequentially. The organic layer was dried with MgSO4, filtered and concentrated. The resulting mixture was purified by silica gel chromatography to obtain the title compound (2.5 g).

Workup

  1. washwashed with an aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-af6c6f8b977b46f984dd9d58390ebc78
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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