HCID 178437761, compound → HCID 178437758, compound

HRID 478067Notes

Reaction equation

HRID 478067 reaction equation
C(C1NC2C=CSC=2C(O)=N1)C.[CH2:13]([CH:15]1[NH:20][C:19]2=[CH:21][S:22][CH:23]=[C:18]2[C:17]([OH:24])=[N:16]1)[CH3:14]>CS(C)=O>[CH2:13]([CH:15]1[N:16]=[C:17]([OH:24])[C:18]2[CH:19]=[CH:21][S:22][C:23]=2[NH:20]1)[CH3:14]

Participants

4

Reactant 2

HCID 178437761HCID 178437761, compoundHCID 178437765HCID 178437765, compound

Product 1

HCID 178437758HCID 178437758, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The aqueous filtrate was extracted with four 75 ml portions of chloroform. The organic extracts were washed once with brine, dried (MgSO4) and concentrated under vacuum. The residual oil was diluted with ether (15 ml) and hexane (15 ml). The solid that crystallized was filtered, washed with four 3 ml portions of ether and combined with the solid obtained earlier from the aqueous solution. The 2.3 g of colorless solid was shown by NMR in DMSO to be a 1:1 mixture of 2-ethyl-4-hydroxy-dihydrothieno-[3,2-d]pyrimidine and 2-ethyl-4-hydroxy-dihydrothieno-[3,4-d]pyrimidine.

Workup

  1. extractionThe aqueous filtrate was extracted with four 75 ml portions of chloroform
  2. washThe organic extracts were washed once with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. additionThe residual oil was diluted with ether (15 ml) and hexane (15 ml)
  6. customThe solid that crystallized
  7. filtrationwas filtered
  8. washwashed with four 3 ml portions of ether
  9. customobtained earlier from the aqueous solution

Sources & evidence

ORD record
ord-4879e9979bf94338baa0871f52f0039b
Source dataset
uspto-grants-1989_12
Patent number
US04889856

Reaction notes

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