Tetrahydrofuran → HCID 69157817, compound

HRID 1394228Notes

Reaction equation

HRID 1394228 reaction equation
Cl[CH:2]1[C:7](SC)([N+:8]([O-:10])=O)[C:6](Cl)=[N:5]C=N1.Cl[C:15]1[N:20]=[C:19]([S:21][CH3:22])[N:18]=[C:17]([NH:23][CH:24]2[CH2:26][CH2:25]2)[C:16]=1[N+:27]([O-])=O.C([N:32](CC)CC)C.O1CCCC1.C1(N)CC1>C(O)C>[CH:24]1([N:23]2[C:2]([C:7]3[C:6]([NH2:32])=[N:5][O:10][N:8]=3)=[N:27][C:16]3[C:17]2=[N:18][C:19]([S:21][CH3:22])=[N:20][CH:15]=3)[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 86760637HCID 86760637, compound

Product 1

HCID 69157817HCID 69157817, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-60 °C

Procedure

(6-Chloro-2-methylsulfanyl-5-nitro-pyrimidine-4-yl)-cyclopropyl-amine 4,6-Dichloro-5-methylsulfanyl-5-nitro-pyrimidine (PCT Int. Appl. (2003), WO 0302544 (14.1 g, 59 mmol), and triethylamine (8.2 ml, 59 mmol) were dissolved in ethanol (400 ml) containing tetrahydrofuran (50 ml) at −60° C. Cycloproplyamine (4.06 ml, 59 mmol) was added dropwise maintaining an internal temperature of −60° C. and stirred slowly to room temperature over 3 hours. The solution was concentrated in vacuo and the residue slurried in diethyl ether. Solid triethylamine hydrochloride was filtered, washed with diethyl ether and the filtrate concentrated in vacuo to afford a crude solid. The solid was purified by column chromatography eluting with a gradient of 40% dichloromethane in hexane to dichloromethane, to afford the title compound (17.89 g, 97%); MS (ES+) m/e 260/262 [M+H]+. Step 2. 6-chloro-N4-cyclopropyl-2-methansulfanyl-pyrimidine-4,5-diamine

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. filtrationSolid triethylamine hydrochloride was filtered
  3. washwashed with diethyl ether
  4. concentrationthe filtrate concentrated in vacuo
  5. customto afford a crude solid
  6. customThe solid was purified by column chromatography
  7. washeluting with a gradient of 40% dichloromethane in hexane to dichloromethane

Sources & evidence

ORD record
ord-2ae2b5e52b114639b42eb4ca7f930e9b
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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