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

HRID 2063515Notes

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

Reactant 4

HCID 284Formic Acid

HCID 702Ethanol

HCID 2723790Thiourea

HCID 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

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

Sources & evidence

ORD record: ord-65a3cdb675ba47b286d6a3afb001b565
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288397B2

Reaction notes

Loading…