Thiourea → HCID 20716446, compound

HRID 1751175Notes

Reaction equation

HRID 1751175 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C[O-].[Na+:7].CN(C)/[CH:10]=[CH:11]/[C:12](=O)[CH:13]([O:16][CH3:17])[O:14][CH3:15]>CO>[CH3:15][O:14][CH:13]([O:16][CH3:17])[C:12]1[CH:11]=[CH:10][N:4]=[C:2]([S-:3])[N:1]=1.[Na+:7]

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamineHCID 10942334Sodium Methoxide

Product 1

HCID 20716446HCID 20716446, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of thiourea (64.7 g, 850 mmol, 1.13 equiv.), sodium methanolate (95%, 40.5 g, 751 mmol, 1.0 equiv.) in methanol (500 mL, 1.5 M) was stirred at room temperature for 30 minutes. A solution of (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (1) (130 g, 751 mmol) in methanol (200 mL) was added and the reaction stirred at room temperature for 2 h. The crude sodium 4-(dimethoxymethyl)pyrimidine-2-thiolate (2) was used directly in the next step without further purification. LC-MS m/z 209 (M+1). Reference: WO 2006/0097341A1, pg 67.

Workup

  1. customThe crude sodium 4-(dimethoxymethyl)pyrimidine-2-thiolate (2) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-1b57f4c49f644aae920900134b4c78a3
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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