Trifluoroacetic acid → 3-[4-(dimethylamino)-7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzyl trifluoroacetate

HRID 1750292Notes

Reaction equation

HRID 1750292 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[C:4]2[C:11]([C:12]3[CH:13]=[C:14]([CH2:18]O)[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:9]([CH2:20][O:21]CC[Si](C)(C)C)[C:5]=2[N:6]=[CH:7][N:8]=1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>>[F:29][C:30]([F:35])([F:34])[C:31]([O:33][CH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:11]2[C:4]3[C:3]([N:2]([CH3:1])[CH3:28])=[N:8][CH:7]=[N:6][C:5]=3[N:9]([CH2:20][OH:21])[CH:10]=2)[CH:13]=1)=[O:32]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706962HCID 86706962, compound

Product 1

HCID 867069633-[4-(dimethylamino)-7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzyl trifluoroacetate

Procedure

A solution of {3-[4-(dimethylamino)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl}methanol (C26) (397 mg, 0.996 mmol) in trifluoroacetic acid (10 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo to provide the product (400 mg) as a brown oil. This material was taken directly into the following step. LCMS m/z 395.1 [M+H+].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5a62403e92fa4f3f82eee7d7d1ace8e2
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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