Lithium iodide → HCID 58459203, compound

HRID 2036608Notes

Reaction equation

HRID 2036608 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:15]([CH:16]3[CH2:18][CH2:17]3)[C:14]3[C:19]([C:23]([O:25]C)=[O:24])=[CH:20][CH:21]=[CH:22][C:13]=3[N:12]=2)[CH3:10])[C:3]=1[C:27]#[N:28].[I-].[Li+]>N1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:15]([CH:16]3[CH2:17][CH2:18]3)[C:14]3[C:19]([C:23]([OH:25])=[O:24])=[CH:20][CH:21]=[CH:22][C:13]=3[N:12]=2)[CH3:10])[C:3]=1[C:27]#[N:28]

Participants

4

Reactant 2

HCID 66321Lithium iodide2×HCID 58459119HCID 58459119, compound

Product 1

HCID 58459203HCID 58459203, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-methyl 2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxylate (137 mg, 0.36 mmol) and lithium iodide (146 mg, 1.1 mmol) in pyridine (5 mL) was heated to reflux at 100° C. for 48 h. Another portion of lithium iodide (146 mg, 1.1 mmol) was added and the mixture was heated at 100° C. for another 48 h. The mixture was concentrated in vacuo, and subjected to the next reaction without further purification: LC-MS (ESI) m/z 364.1 [M+H]+.

Workup

  1. temperaturethe mixture was heated at 100° C. for another 48 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customsubjected to the next reaction without further purification

Sources & evidence

ORD record
ord-9bca371f32764813b53ce2deefd7e0d7
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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