Formaldehyde → HCID 86684128, compound

HRID 1024029Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.C=O.[BH3-][C:27]#N.[Na+]>CO>[Br:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:19][CH2:20][N:21]([CH3:27])[CH2:22][CH2:23]3)=[CH:14][N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 106b (210 mg, 0.52 mmol), formaldehyde (150 mg, 5 mmol), and NaBH3CN (220 mg, 3.5 mmol) in methanol (8 mL) was stirred at 20° C. for 3 hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column-chromatography eluting with CH2Cl2/methanol (20:1) to afford 106c (200 mg, 90%). MS: [M+H]+ 388.

Workup

customThe solid was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column-chromatography
washeluting with CH2Cl2/methanol (20:1)

Sources & evidence

ORD record: ord-403d5efa70f04b0094caa490a6d5247a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722676B2

Reaction notes

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