Ammonia → HCID 15405115, compound

HRID 351997Notes

Reaction equation

[NH3:1].[CH3:2][O:3][C:4]1[CH:42]=[CH:41][C:7]([C:8]([O:23][CH2:24][C@H:25]2[O:29][C@@H:28]([N:30]3[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]3=[O:32])[CH2:27][C@:26]32[CH2:40][O:39]3)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[CH:14]=[CH:13][C:12](OC)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[CH3:43][OH:44]>>[CH3:43][O:44][C:12]1[CH:11]=[CH:10][C:9]([C:8]([O:23][CH2:24][C@H:25]2[O:29][C@@H:28]([N:30]3[CH:38]=[C:36]([CH3:37])[C:34](=[O:35])[NH:33][C:31]3=[O:32])[CH2:27][C@:26]2([CH2:40][NH2:1])[OH:39])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[CH:41]=[CH:42][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)=[CH:14][CH:13]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol2×

HCID 15405113HCID 15405113, compound

Product 1

HCID 15405115HCID 15405115, compoundYield 45%

Procedure

A saturated solution of ammonia in methanol (9 ml) was added to a solution of 5′-O-(4,4′-dimethoxytrityl)-3′-C,O-methylenethymidine (901 mg; 1.62 mmol) in methanol (3 ml), and the resulting solution stood at room temperature for 3 days. Excess ammonia and methanol was evaporated and the residue purified by chromatography (CH3OH-Hexanes-CHCl3, 1:1:8) to yield 414 mg (45%) of 5′-O-(4,4′-dimethoxytrityl)-3′-C-aminomethylthymidine as a colorless solid.

Workup

customExcess ammonia and methanol was evaporated
customthe residue purified by chromatography (CH3OH-Hexanes-CHCl3, 1:1:8)

Sources & evidence

ORD record: ord-0bf612d1761943548d7d16a4bd796a75
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743902B1

Reaction notes

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