Sodium hydride → 5-(4-benzyloxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51486Notes

Reaction equation

HRID 51486 reaction equation
S(O[CH:12]1[CH2:16][CH2:15][O:14][CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:39]3[C:38]([NH2:40])=[N:37][CH:36]=[N:35][C:34]=3[NH:33][CH:32]=2)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+]>CN(C)C=O>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[C:39]3[C:38]([NH2:40])=[N:37][CH:36]=[N:35][C:34]=3[N:33]([CH:12]3[CH2:16][CH2:15][O:14][CH2:13]3)[CH:32]=2)=[CH:29][CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateHCID 227361705-(4-benzyloxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227364065-(4-benzyloxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 2, 3-tosyloxytetrahydrofuran (1.84 g) was reacted with 5-(4-benzyloxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (2.9 g) using sodium hydride (0.30 g, of a 60% dispersion in mineral oil) and dimethylformamide (40 ml) except that the mixture was heated for 4.5 hours at 90° C. to give 5-(4-benzyloxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine as a solid.

Sources & evidence

ORD record
ord-c552f0f181c8468ca09efb8097fa2589
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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