Ammonium Hydroxide → 59652-80-1

HRID 2191032Notes

Reaction equation

C([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:29])([OH:28])[OH:27])[C@@H:21]([OH:30])[C@H:20]1[OH:31])(=O)C1C=CC=CC=1.[NH4+].[OH-]>>[NH2:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:27])([OH:28])[OH:29])[C@@H:21]([OH:30])[C@H:20]1[OH:31]

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 59289287HCID 59289287, compound

Product 1

HCID 4977371359652-80-1Yield 70%

Procedure

Compound 24.3 (43 mg, 0.961 mmol) was treated with concentrated NH4OH (4.85 mL, 0.02 M) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was treated with 1% AcOH (2 mL). Reverse phase HPLC afforded compound 24.4 (23 mg, 70% yield) as a white solid: 1H NMR (D2O, 300 MHz) 8.21 (s, 1H), 8.11 (s, 1H), 6.41 (m, 1H), 5.97 (d, J=5.7 Hz, 1H), 5.84 (m, 1H), 4.66 (appt t, J=4.8 Hz, 1H), 4.53 (m, 1H), 4.22 (t, J=4.8 Hz, 1H); 31P NMR (D2O, 121.4 MHz) 9.4; MS (ESI) m/z 344 [M+H]+.

Workup

customThe solvent was removed in vacuo
additionthe residue was treated with 1% AcOH (2 mL)

Sources & evidence

ORD record: ord-6ab6f07b232b452097208cccb2591048
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324179B2

Reaction notes

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