Potassium Hydroxide → 4-(1,3-Dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)-6-((1-methylisoquinolin-6-yl)ethynyl)pyridin-2-amine

HRID 923672Notes

Reaction equation

HRID 923672 reaction equation
C(OC(=O)N(C(C(=O)[NH:12][C:13]1[CH:18]=[C:17]([C:19]2[C:20]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH:16]=[C:15]([C:30]#[C:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[C:38]([CH3:42])=[N:37][CH:36]=[CH:35]3)[N:14]=1)C)C)(C)(C)C.[H][H].[OH-].[K+]>>[CH3:28][N:27]1[C:20]2[C:19]([C:17]3[CH:16]=[C:15]([C:30]#[C:31][C:32]4[CH:33]=[C:34]5[C:39](=[CH:40][CH:41]=4)[C:38]([CH3:42])=[N:37][CH:36]=[CH:35]5)[N:14]=[C:13]([NH2:12])[CH:18]=3)=[N:24][CH:23]=[N:22][C:21]=2[C:25]([CH3:29])=[N:26]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 178432658tert-butyl-N-{1-[(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate H2

Product 1

HCID 1179028684-(1,3-Dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)-6-((1-methylisoquinolin-6-yl)ethynyl)pyridin-2-amine

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl-N-{1-[(4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate H2 (150 mg, 0.31 mmol) and potassium hydroxide (1 mol/l solution in MeOH:water=2:1, 3 ml, 3 mmol) is stirred at 60° C. for 2 days. The precipitate is collected and purified by NP chromatography to yield 4-{1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-[2-(1-methylisoquinolin-6-yl)ethynyl]pyridin-2-amine. Yield: 110 mg (89%). HPLC-MS: M+H=406; tR=1.07 min (METHOD—1).

Workup

  1. customThe precipitate is collected
  2. custompurified by NP chromatography

Sources & evidence

ORD record
ord-02f9d65122ee4fa4ae9371edbb91813e
Source dataset
uspto-grants-2016_03
Patent number
US09278978B2

Reaction notes

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