Methanesulfonyl chloride → HCID 59184747, compound

HRID 426262Notes

Reaction equation

HRID 426262 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]([C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=3)[C:20]#[N:21])=[O:16])=[C:13]([CH:26]([CH3:28])[CH3:27])[C:12](=[O:29])[NH:11][C:10]2=[O:30])[CH:5]=[C:4]([F:31])[N:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1>[C:20]([C:19]1[CH:18]=[C:17]([CH:24]=[C:23]([CH3:25])[CH:22]=1)[C:15]([C:14]1[N:9]([CH2:8][C:6]2[CH:5]=[C:4]([F:31])[N:3]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:7]=2)[C:10](=[O:30])[N:11]([S:33]([CH3:32])(=[O:35])=[O:34])[C:12](=[O:29])[C:13]=1[CH:26]([CH3:28])[CH3:27])=[O:16])#[N:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 46880493HCID 46880493, compound

Product 1

HCID 59184747HCID 59184747, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-[3-(2-Amino-6-fluoro-pyridin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile (86 mg, 0.204 mmol) was dissolved in 5 mL THF. TEA (0.31 μl, 12 eq.) was added and the reaction was stirred at 0° C. for 10 minutes. MsCl (158 μl, 10 eq.) was added. The reaction was stirred at 0° C. for 40 minutes. The reaction crude was concentrated down and purified (silica gel, 0-80% EtOAC/hexane) to give white powder (89 mg, 75%). LC-MS shows 578.0 (M+1). 1H NMR (300 MHz, CDCl3): δ 9.6 (s, 1H), 7.98 (s, 1H), 7.83 (s, 1H), 7.76 (s, 1H), 7.07 (s, 1H), 6.83 (s, 1H), 4.82 (dd, 2H), 3.63 (s, 3H), 3.56 (s, 3H), 2.43 (s, 3H), 2.22 (m, 1H), 1.22 (dd, 6H).

Workup

  1. stirringThe reaction was stirred at 0° C. for 40 minutes
  2. customThe reaction crude
  3. concentrationwas concentrated down
  4. custompurified (silica gel, 0-80% EtOAC/hexane)

Sources & evidence

ORD record
ord-b8ddc26e67af4a37b4100b3b43df1125
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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