Formic Acid → 2-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine

HRID 60189Notes

Reaction equation

HRID 60189 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=O)[CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[C:6](Cl)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.NC(N)=[S:25].[CH3:27][CH2:28][OH:29].[CH:30]([OH:32])=O>>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:30]([OH:32])[C:7]=2[N:8]=1.[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[CH2:10][C:9]1[S:25][C:2]2[N:3]=[C:4]([S:21][CH3:22])[N:5]=[C:6]([O:29][CH2:28][CH3:27])[C:7]=2[N:8]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 2723790ThioureaHCID 57742481HCID 57742481, compound

Product 2

HCID 685191702-(2,6-Dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidineYield 41%HCID 178503525HCID 178503525, compoundYield 18%

Conditions

Temperature
90 °C

Procedure

To a mixture of N-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-2-(2,6-dichloro-phenyl)-acetamide (10 g, 25 mmol), thiourea (1.9 g, 25 mmol), and EtOH (100 mL) was added formic acid (0.8 mL) at rt. The resulting mixture was heated to 90° C. After 12 h, the reaction mixture was cooled and concentrated. The resulting residue was collected by vacuum filtration and washed with H2O (50 mL) followed by hexanes (50 mL). The title compound purified by FCC to afford 2-(2,6-dichloro-benzyl)-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-7-ol (1.6 g, 18%) and 2-(2,6-dichloro-benzyl)-7-ethoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidine (4 g, 41%) as colorless solids.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe resulting residue was collected by vacuum filtration
  4. washwashed with H2O (50 mL)
  5. customThe title compound purified by FCC

Sources & evidence

ORD record
ord-593e427655594fdaa06c8697a1ea3ecc
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Reaction notes

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