Formic Acid → 2-(methylthio)thiazolo[4,5-d]pyrimidin-7(6h)-one

HRID 2408985Notes

Reaction equation

HRID 2408985 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([S:9][CH3:10])[S:5][C:6]=1[C:7]#[N:8].S(=O)(=O)(O)O.[OH2:16].[CH:17](O)=O>>[CH3:10][S:9][C:4]1[S:5][C:6]2[C:7](=[O:16])[NH:8][CH:17]=[N:1][C:2]=2[N:3]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 6764114-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile

Product 1

HCID 1355006902-(methylthio)thiazolo[4,5-d]pyrimidin-7(6h)-oneYield 88%

Conditions

Temperature
95 °C

Procedure

To a solution of 4-amino-2-(methylthio)thiazole-5-carbonitrile (800 mg) in formic acid (8 mL) was added concentrated sulfuric acid (3.2 mL) dropwise for 15 min. The reaction mixture was stirred at 90-100° C. for 1 h and allowed to rt. The reaction mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with water and dried to give the product as a white color solid (820 mg, 88%), mp 260-262° C. 1H NMR (400 MHz, DMSO-d6): δ 12.83 (1H, br s), 8.25 (1H, s), 2.80 (3H, s); LC-MS (negative ion mode): m/z 198 (M−H)−.

Workup

  1. customallowed to rt
  2. additionThe reaction mixture was poured into ice
  3. stirringstirred for 15 min
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f4a9aecde27d4b559a81ce5ca51b0ff3
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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