Sodium Iodide → Propan-2-yl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 2279913Notes

Reaction equation

HRID 2279913 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:39]=[CH:38][C:27]([CH2:28][P:29](=[O:37])([O:33][CH:34]([CH3:36])[CH3:35])[O:30]CC)=[CH:26][C:25]=3[O:40][CH3:41])[N:14]=2)=[CH:4][CH:3]=1.[I-].[Na+]>N1C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:39]=[CH:38][C:27]([CH2:28][P:29](=[O:30])([OH:37])[O:33][CH:34]([CH3:35])[CH3:36])=[CH:26][C:25]=3[O:40][CH3:41])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86697852Ethyl propan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate2×

Product 1

HCID 86697851Propan-2-yl hydrogen (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A solution of ethyl propan-2-yl (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate (Compound 72C, 550.0 mg, 0.83 mmol) in pyridine (5.50 mL) was charged with sodium iodide (748 mg, 4.99 mmol). The reaction was heated at 120° C. for 24 hours.

Sources & evidence

ORD record
ord-32d62d88558643a0b40983059cb6725c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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