Ammonium Hydroxide → 1,1-dimethylethyl 4-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate

HRID 1909984Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To 1,1-dimethylethyl 4-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate (313 mg, 0.753 mmol) was added ammonium hydroxide (2 mL, 51.4 mmol) and 1,4-Dioxane (1 mL) to a 5 mL microwave vial and heated in microwave for 20 min. at 100° C. After total of 35 minutes the reaction was completed. The reaction was concentrated to give 1,1-dimethylethyl 4-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate (336 mg). 1H NMR (400 MHz, DMSO-d6) δ 8.09 (s, 1H), 7.60 (s, 1H), 4.71 (tt, J=5.40, 10.64 Hz, 1H), 4.08 (br. s., 2H), 2.91 (br. s., 2H), 1.81-1.94 (m, 4H), 1.43 (s, 9H).

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-2f2bbdb3f8bb47a79ce88203a83d03a3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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