Lawesson's reagent → HCID 117653766, compound

HRID 510470Notes

Reaction equation

HRID 510470 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH:10]=O)=[C:4](Cl)[N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1COCC1>[Cl:8][C:6]1[C:5]2[N:9]=[CH:10][S:22][C:4]=2[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide

Product 1

HCID 117653766HCID 117653766, compoundYield 124.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (12 g, 57 mmol) in THF (250 mL) was added Lawesson's reagent (17.5 g, 43 mmol). The reaction mixture was stirred at 65° C. for 30 minutes. The reaction mixture was then filtered, and the filtrate was concentrated. The crude yellow solid obtained was triturated using diethyl ether to afford the title compound (10 g, 93.4%) as a pale yellow solid. LCMS (ES+) 186.95 (M+H)+, RT 1.31 minutes (method 1).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude yellow solid obtained
  4. customwas triturated

Sources & evidence

ORD record
ord-aeee374269bd4fba8456757ba71838be
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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