Sodium Bicarbonate → HCID 89871000, compound

HRID 516177Notes

Reaction equation

[CH3:1][NH:2][CH3:3].C1COCC1.[C:9]([O:13][C:14]([N:16]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:17]1[C:18]2[C:25]([I:26])=[CH:24][N:23]([C@@H:27]3[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:29]([CH:39]=O)[CH2:28]3)[C:19]=2[N:20]=[CH:21][N:22]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:44]([O:43][C:41]([N:16]([C:14]([O:13][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:15])[C:17]1[C:18]2[C:25]([I:26])=[CH:24][N:23]([C@@H:27]3[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[C@H:29]([CH2:39][N:2]([CH3:3])[CH3:1])[CH2:28]3)[C:19]=2[N:20]=[CH:21][N:22]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

Conditions

Temperature: 0 °C

Procedure

A 1M dimethylamine THF solution (0.3 ml) and acetic acid (0.2 ml) were added to a solution of (2S,4S)-tert-butyl 4-(4-(bis(tert-butoxycarbonyl)amino)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-formylpyrrolidine-1-carboxylate (68 mg) obtained in Step 5 in methylene chloride (2 ml), and the resulting mixture was cooled to 0° C. Sodium triacetoxyborohydride (127 mg) was added to the reaction mixture, and stirred at 0° C. for 2 hours. The reaction mixture was neutralized using a sodium hydrogen carbonate aqueous solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-yellow, amorphous substance (31.9 mg). Physical properties: m/z [M+H]+ 687.2

Workup

dry with materialthe organic layer was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-8401ce261b534e42aa6b81e09f11417e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108973B2

Reaction notes

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