Sodium hydride → 4-amino-5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51480

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[C:5]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.S(O[CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[O:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]2[C:5]3[C:4]([NH2:3])=[N:9][CH:8]=[N:7][C:6]=3[N:10]([CH:37]3[CH2:41][CH2:40][O:39][CH2:38]3)[CH:11]=2)=[CH:18][CH:17]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Sodium hydride (120 mg, of a 60% dispersion in mineral oil) was added to a solution of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (906 mg) and dimethylformamide (30 ml) with stirring under nitrogen. The mixture was stirred for 30 minutes and then a solution of 3-(tosyloxy) tetrahydrofuran (750 mg) in dimethyl formamide (10 ml) was added with stirring. The mixture was stirred and heated at 95° C. for 18 hours and then evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried and evaporated to give a residual gummy solid which was triturated with ether and filtered to give 5-(4-phenoxyphenyl)-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine m.p. 196-196.5° C.

Workup

stirringThe mixture was stirred for 30 minutes
stirringwith stirring
stirringThe mixture was stirred
customevaporated under vacuum
customThe residue was partitioned between ethyl acetate and water
customThe ethyl acetate layer was separated
customdried
customevaporated
customto give a residual gummy solid which
customwas triturated with ether
filtrationfiltered

Sources & evidence

ORD record: ord-7a4d91e2f8894e729bbc93864baa2b96
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Linked notes

Loading…