HCID 58169499, compound → HCID 50943143, compound

HRID 1484852Notes

Reaction equation

HRID 1484852 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][N:13]=[C:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1>CO.[OH-].[Na+]>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([C:16]#[CH:17])=[CH:14][N:13]=[C:12]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58169499HCID 58169499, compound

Product 1

HCID 50943143HCID 50943143, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To the solution of crude N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenyl-5-((trimethylsilyl)ethynyl) pyrimidin-4-amine in MeOH (3 mL), 20% NaOH was added until the pH was adjusted to 12. After stirring at rt for 15 min, the reaction mixture was evaporated to dryness and purified by silica gel chromatography (hexane/EtOAc=3:1-1:1 as eluent) to afford N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-ethynyl-2-phenylpyrimidin-4-amine (Compound 14) (71 mg, 48%). LC-MS (m/z): 302.1 [M+H]+. 1H NMR (300 MHz, DMSO-d6): δ 0.71-0.76 (m, 2H), 0.94-1.01 (m, 2H), 1.90-1.99 (m, 1H), 6.18-6.28 (bs, 1H), 7.06-7.10 (bs, 1H), 7.51-7.53 (m, 3H), 8.34-8.39 (m, 3H), 9.86 (s, 1H), 12.10 (s, 1H).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. custompurified by silica gel chromatography (hexane/EtOAc=3:1-1:1 as eluent)

Sources & evidence

ORD record
ord-5537dce049aa448a9fe10a3a0bfc1f66
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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