Sodium Hydroxide → HCID 21220605, compound

HRID 1584852Notes

Reaction equation

HRID 1584852 reaction equation
[C:1]([CH2:5][C:6]([O:8]CC)=O)(=O)[CH2:2][CH3:3].COC(OC)N(C)C.[CH3:19][CH2:20][O-].[Na+].[CH2:23]([C:25]1[C:30](C(OCC)=[S:32])=CN=C(C)N=1)[CH3:24].[OH-].[Na+].C([C:41]1C(C(O)=S)=C[N:44]=[C:43]([CH3:50])[N:42]=1)C.C(Cl)(=O)C(Cl)=O.C(C1C(C(Cl)=O)=[CH:63][N:62]=[C:61]([S:68][CH3:69])[N:60]=1)C.C1([Mg]Br)C=CC=CC=1>O>[C:6]([C:5]1[C:1]([CH2:2][CH3:3])=[N:60][C:61]([S:68][CH3:69])=[N:62][CH:63]=1)(=[O:8])[C:20]1[CH:19]=[CH:30][CH:25]=[CH:23][CH:24]=1.[CH2:2]([C:1]1[C:5]([C:6]([OH:8])=[S:32])=[CH:41][N:42]=[C:43]([CH3:50])[N:44]=1)[CH3:3]

Participants

12

Reactant 9

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 78373Dimethylformamide dimethyl acetalHCID 78656Ethyl 3-oxovalerateHCID 2723922Sodium ethoxideHCID 212206254-Ethyl-2-(methylthio)-5-pyrimidinecarbonyl chlorideHCID 86754397HCID 86754397, compoundHCID 178418255HCID 178418255, compoundHCID 178437670HCID 178437670, compound

Product 2

HCID 21220605HCID 21220605, compoundHCID 178437670HCID 178437670, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared by (a) reaction of ethyl propionylacetate (19.4 g, 0.13 mol) and N,N-dimethylformamide dimethyl acetal (16.0 g, 0.13 mol) in analogy to Example 67, (b) reaction with NaOEt (0.18 mol) and S-methyl isothouronium sulfate (18.7 g, 0.067 mol) also described for Example 67, (c) hydrolysis of the ethyl 4-ethyl-2-methylthiopyrimidine-5-carboxylate (18.0 g, 0.08 mmol) with NaOH (12.7 g, 0.32 mol) in H2O (200 mL) as described in Example 67, (d) reaction of the 4-ethyl-2-methylthiopyrimidine-5-carboxylic acid (0.50 g, 2.5 mmol) and oxalyl chloride (0.32 g, 2.5 mmol) as described in Example 11, and (e) reaction of the 4-ethyl-2-methylthiopyrimidine-5-carbonyl chloride (0.50 g, 2.3 mmol) and phenyl magnesium bromide as described for Example 23, resulting in a yield of 22% (0.14 g) from the 4-ethyl-2-methylthiopyrimidine-5-carboxylic acid;); 1H NMR (CDCl3) δ 9.18 (s, 1H), 7.80 (d, 2H), 7.62 (t, 1H), 7.50 (t, 2H), 2.81 (q, 2H), 2.61 (s, 3H), 1.22 (t, 3H).

Sources & evidence

ORD record
ord-5c8b907bf9a0470699a6e362be03e448
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

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