Diethyl Ether → HCID 178464161, compound

HRID 630085Notes

Reaction equation

HRID 630085 reaction equation
C[Mg]Br.C([O:6][CH2:7][CH3:8])C.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[CH2:23][S:24][C:25]1[N:30]=[C:29](O)[CH:28]=C(C)[N:26]=1)[C:18]#[N:19]>C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([C:18](=[NH:19])[N:11]([CH2:12][CH3:13])[CH2:9][CH3:10])[CH:20]=[CH:21][C:22]=1[CH2:23][S:24][C:25]1[N:26]=[C:7]([OH:6])[CH:8]=[C:29]([CH3:28])[N:30]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8021DiethylamineHCID 178418573HCID 178418573, compoundHCID 178429438HCID 178429438, compound

Product 1

HCID 178464161HCID 178464161, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 3.0 M methyl magnesium bromide in diethyl ether (1.3 mL, 3.86 mmol) dissolved in anhydrous THF (4 mL) was added diethyl amine in anhydrous THF (1 mL). The mixture was stirred for 15 minutes at 40° C. Then, 3-chloro-4-{[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]methyl}benzonitrile (375 mg, 1.3 mmol) was added and stirred at 40° C. for 3.5 hours. The solvent was evaporated, and the residue was dissolved in DCM and purified on silica gel using 20% DCM/MeOH to afford 3-chloro-N,N-diethyl-4-{[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]methyl}benzene-1-carboximidamide (111 mg, 15% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.15 (t, J=7.9 Hz, 6H), 2.21 (s, 3H), 2.90 (q, J=7.2 Hz, 4H), 4.51 (s, 2H), 6.0 (bs, 1H), 7.51-7.54 (m, 1H), 7.81-7.84 (m, 2H); LRMS (ES+) m/z 365 (100%, M+1).

Workup

  1. stirringstirred at 40° C. for 3.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. custompurified on silica gel using 20% DCM/MeOH

Sources & evidence

ORD record
ord-caf713a29aac43c2abb3e882bf88919c
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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