Diiodomethane → HCID 44227709, compound

HRID 1907842Notes

Reaction equation

N(OCCC(C)C)=O.[N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][N:20]3[C:24]4[N:25]=[C:26](N)[N:27]=[CH:28][C:23]=4[N:22]=[N:21]3)=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C(I)[I:31]>>[I:31][C:26]1[N:27]=[CH:28][C:23]2[N:22]=[N:21][N:20]([CH2:19][C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[N:9]=[CH:10][CH:11]=[CH:12]4)[C:24]=2[N:25]=1

Participants

Reactant 3

HCID 6346Diiodomethane

HCID 8053Isoamyl Nitrite

HCID 44227708HCID 44227708, compound

Product 1

HCID 44227709HCID 44227709, compoundYield 40%

Conditions

Temperature: 85 °C

Procedure

Isoamyl nitrite (0.78 mL) was added to a suspension of 3-(quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine (102 mg, 0.370 mmol) in CH2I2 (2.4 mL) under a nitrogen atmosphere. The mixture was stirred at 85° C. for 1 h. The solvent was removed under reduced pressure. Flash chromatography of the resulting residue over silica gel to afford the desired product (57 mg, 40%). 1H NMR (300 MHz, CDCl3) δ 6.03 (s, 2H), 7.44 (m, 1H), 7.79-8.18 (m, 4H), 8.94 (m, 1H), 9.27 (s, 1H); LCMS (APCI) m/z 389.0 (M+H+).

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-46e2ec93972b48d7961361b966a6e37c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598184B2

Reaction notes

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