Triethylamine → HCID 178473466, compound

HRID 471499Notes

Reaction equation

HRID 471499 reaction equation
[NH2:1][C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([CH3:13])[S:9][C:4]=2[NH:5][C:6](=[S:8])[N:7]=1.CCN(CC)CC.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C.CCOC(C)=O>[CH3:12][C:11]1[C:3]2[C:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])=[N:7][C:6](=[S:8])[NH:5][C:4]=2[S:9][C:10]=1[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178435041HCID 178435041, compound

Product 1

HCID 178473466HCID 178473466, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-thione (211 mg, 1 mmol) in DMF (5 mL) was added Et3N (0.21 mL, 1.5 mmol) and ethyl chloroformate (0.143 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and evaporated. The residue was purified on Biotage SP-1 eluting with EtOAc/hexane to give the title compound (154 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ 1.22 (t, J=7.2 Hz, 3H), 2.38 (s, 3H), 2.39 (s, 3H), 4.25 (q, J=7.2 Hz, 2H), 7.25-7.21 (m, 2H). MS 284 (MH+)

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on Biotage
  6. washSP-1 eluting with EtOAc/hexane

Sources & evidence

ORD record
ord-cffee9e65b4040e19fe7741b538ccefd
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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