(2-Methylphenyl)methanethiol → 1-methyl-8-((2-methylbenzyl)thio)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 920412Notes

Reaction equation

HRID 920412 reaction equation
Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[C:14]1([CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][SH:21].CC(C)([O-])C.[K+]>O1CCCC1>[CH3:11][N:7]1[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=[C:2]([S:21][CH2:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:22])[CH:12]=[C:6]12

Participants

5

Reactant 3

HCID 288028(2-Methylphenyl)methanethiolHCID 23665647Potassium tert-butoxideHCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Product 1

HCID 712367631-methyl-8-((2-methylbenzyl)thio)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-oneYield 15.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (200 mg, 1.002 mmol) and o-tolylmethanethiol (166 mg, 1.202 mmol) in tetrahydrofuran (THF) (5 mL) stirred in air at room temperature was added potassium tert-butoxide (112 mg, 1.002 mmol) in one charge. The reaction mixture was stirred at rt for 3 hr. The resulting mixture was concentrated and purified by prep-HPLC to give 50 mg 1-methyl-8-((2-methylbenzyl)thio)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (50 mg, 0.158 mmol, 15.73% yield).

Workup

  1. additioncharge
  2. stirringThe reaction mixture was stirred at rt for 3 hr
  3. concentrationThe resulting mixture was concentrated
  4. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-e0aa4e40a1f24b67b3274c52547c02a7
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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