Triethylamine → (S)-7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one

HRID 2171341Notes

Reaction equation

HRID 2171341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([C@@H:10]([CH3:13])[CH2:11]O)[CH3:9])[NH:5][C:4](=[O:14])[N:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([CH3:9])[C@@H:10]([CH3:13])[CH2:11][N:5]2[C:4](=[O:14])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178461810(S)-4-chloro-6-((1-hydroxypropan-2-yl)(methyl)amino)pyrimidin-2(1H)-one

Product 1

HCID 86728322(S)-7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-chloro-6-((1-hydroxypropan-2-yl)(methyl)amino)pyrimidin-2(1H)-one (700 mg, 3.22 mmol) and triethylamine (1.35 mL, 9.65 mmol) in tetrahydrofuran (THF) (20 mL) was added methanesulfonyl chloride (0.508 mL, 6.43 mmol) at 0° C. The reaction mixture was stirred at room temperature for 16 h and concentrated. Purification via Prep-HPLC (column: YMC-Actus Triart C18 150×30 mm; 2 M NH3 in methanol) afforded the title product.

Workup

  1. concentrationconcentrated
  2. customPurification via Prep-HPLC (column: YMC-Actus Triart C18 150×30 mm; 2 M NH3 in methanol)

Sources & evidence

ORD record
ord-b5eeaa1f30b34377b433f5c4d434e18a
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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