Ammonia → HCID 89423130, compound

HRID 1752418Notes

Reaction equation

HRID 1752418 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([N:12]([CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)[S:13]([CH3:16])(=[O:15])=[O:14])[N:3]=1.[NH3:25]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:25])=[O:9])[CH:5]=[C:4]([N:12]([CH2:17][CH:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)[S:13]([CH3:16])(=[O:15])=[O:14])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 89423187HCID 89423187, compound

Product 1

HCID 89423130HCID 89423130, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of methyl 2-chloro-6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methylsulfonamido)pyrimidine-4-carboxylate (0.911 g, 2.40 mmol) in MeOH (10 mL) was added 7M ammonia in MeOH (10 mL, 70 mmol). It started as a suspension, then dissolved, and then gave a precipitate. After 3 h the solid was filtered, rinsed once with 5 mL MeOH and air-dried to give the product 2-chloro-6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methylsulfonamido)pyrimidine-4-carboxamide as a white powder (0.715 g, 1.96 mmol, 82% yield). LC/MS: m/z=365.2 [M+H]+.

Workup

  1. dissolutiondissolved
  2. customgave a precipitate
  3. filtrationAfter 3 h the solid was filtered
  4. washrinsed once with 5 mL MeOH
  5. customair-dried

Sources & evidence

ORD record
ord-d7102d154fb3412daca6821b0544d98e
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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