Sodium Acetate → HCID 9931357, compound

HRID 2082022Notes

Reaction equation

HRID 2082022 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[N:8]=[C:9](Cl)[C:10]2[S:15][CH:14]=[CH:13][C:11]=2[N:12]=1.Cl.[CH3:18][O:19][C:20]([C:22]1[C:23]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=2)=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21]>O1CCCC1>[CH3:18][O:19][C:20]([C:22]1[C:23]([C:28]2[CH:29]=[CH:30][C:31]([CH2:34][NH:35][C:9]3[C:10]4[S:15][CH:14]=[CH:13][C:11]=4[N:12]=[C:7]([Cl:6])[N:8]=3)=[CH:32][CH:33]=2)=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidineHCID 21988960HCID 21988960, compound

Product 1

HCID 9931357HCID 9931357, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium acetate (1.2 g), 2,4-dichlorothieno[3,2-d]pyrimidine(0.75 g) and 4'-aminomethyl(1,1'-biphenyl)-2-carboxylic acid methylester hydrochloride (1.02 g) were suspended in 40 mL of tetrahydrofuran. The reaction mixture was stirred at room temperature for 3 days at which time all the THF was removed by evaporation. The residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel chromatography (ETOAc/Hexane) to yield the product as a buff powder (0.81 g, 54%) (m.p.=177°-182° C.): 1H NMR (DMSO-d6, 400 MHz) δ8.98 (t, J=6.0 Hz, 1H), 8.19 (d, J=5.4 Hz, 1H), 7.71 (dd, J=1.1; 7.7 Hz, 1H), 7.60 (m, 1H), 7.46 (m, 1H), 7.38 (m, 4H), 7.25 (m, 2H), 4.73 (d, J=5.9 Hz, 2H), 3.58 (s, 3H); positive FAB MS m/e 410 (MH); 376 (M--Cl+H).

Workup

  1. customwas removed by evaporation
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel chromatography (ETOAc/Hexane)

Sources & evidence

ORD record
ord-4688fec8ea9e4b14a2a1719f18ed54bd
Source dataset
uspto-grants-1993_02
Patent number
US05187168

Reaction notes

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