Diethyl Malonate → HCID 178477516, compound

HRID 44443Notes

Reaction equation

HRID 44443 reaction equation
C(C1N=[C:12]([OH:14])[CH:11]=[C:10]([OH:15])N=1)C1C=CC=CC=1.Cl.[CH2:17]([S:19][CH:20]([S:24][CH2:25][CH3:26])[C:21]([NH2:23])=[NH:22])[CH3:18].C(OCC)(=O)CC(OCC)=O>>[CH2:17]([S:19][CH:20]([S:24][CH2:25][CH3:26])[C:21]1[N:23]=[C:12]([OH:14])[CH:11]=[C:10]([OH:15])[N:22]=1)[CH3:18]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 86688160HCID 86688160, compoundHCID 178516645HCID 178516645, compound

Product 1

HCID 178477516HCID 178477516, compound

Procedure

Prepared in a manner similar to 2-benzylpyrimidine-4,6-diol using 2,2-bis(ethylthio)acetamidine hydrochloride 4 and diethyl malonate as the starting materials to yield a dark yellow waxy solid. MS: (ESI, Neg) m/z 245.3 (M−1). H1 NMR: 11.7 ppm (d) 2H. 5.2 ppm (s) 0.69H. 4.8 ppm (s) 1H. 2.65 ppm (m) 4H. 1.17 ppm (t) 6H. Subsequent sulfanyl oxidation can be used to generate various Y moieties, C(O), etc., as described above.

Workup

  1. customto yield a dark yellow waxy solid

Sources & evidence

ORD record
ord-450cb1fb25524b1aa9ab7aa5c55fc677
Source dataset
uspto-grants-2013_09
Patent number
US08541431B2

Reaction notes

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