Ammonium Hydroxide → HCID 178480949, compound

HRID 51590

Reaction equation

[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[NH4+:26]>O1CCOCC1>[ClH:1].[I:11][C:10]1[C:3]2[C:2]([NH2:26])=[N:7][CH:6]=[N:5][C:4]=2[N:8]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of trans-4-chloro-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidine (750 mg, 1.63 mmol) and 1,4-dioxane (10 mL) and 30% aqueous ammonium hydroxide (10 mL) was heated at 120° C. in a sealed tube for 18 hours. The mixture is cooled and lyophilized to give trans-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine hydrochloride (750 mg, quantitative): 1H NMR (DMSO-d6, 400 MHz) δ 10.2 (bs, 1H), 8.08(s, 1H), 7.53(s, 1H), 6.59(bs, 2H), 4.50(m, 1H), 2.5-3.2 (m, 9H), 2.51(s, 3H), 1.8-2.0(m, 6H), 1.46 (m, 2H); MS MH+441.2; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 3.85 min.

Workup

temperatureThe mixture is cooled

Sources & evidence

ORD record: ord-48c24f40ace44a39869a611e4070494c
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Linked notes

Loading…