Sodium Hydroxide → (6-Chloro-2-methylpyrimidin-4-yl)thiourea

HRID 1191161Notes

Reaction equation

HRID 1191161 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12]C(=O)OCC)=[S:11])[CH:3]=1.[OH-].[Na+]>>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86600832Ethyl 6-chloro-2-methylpyrimidin-4-ylcarbamothioylcarbamate

Product 1

HCID 57562811(6-Chloro-2-methylpyrimidin-4-yl)thioureaYield 91.3%

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 6-chloro-2-methylpyrimidin-4-ylcarbamothioylcarbamate (275 mg, 1.0 mmol) and 1N sodium hydroxide (3.5 eq) was heated and stirred at 50° C. for 2 h. The resulting slurry was cooled to 20-22° C. The solid was collected by vacuum filtration, washed with water, and dried to give 185 mg of 1-(6-chloro-2-methylpyrimidin-4-yl)thiourea (91% yield). 1H NMR (400 MHz, DMSO-d6): δ2.51 (S, 3H), 7.05 (s, 1H), 9.35 (s, 1H), 10.07 (s, 1H), 10.91 (s, 1H); 13C NMR (125 MHz, DMSO-d6) δ: 25.25, 104.56, 159.19, 159.33, 167.36, 180.91.

Workup

  1. temperatureThe resulting slurry was cooled to 20-22° C
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1884dd956ce547fda9a0eb3105e641ed
Source dataset
uspto-grants-2014_03
Patent number
US08680103B2

Reaction notes

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