Potassium Carbonate → 4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-6-pyrrolidin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine

HRID 722246Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[CH:20]=[C:19]([CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[NH:18][C:4]=2[N:5]=[C:6]([NH:8]C(=O)CCCCCCC)[N:7]=1.Cl[CH2:28][C:29]1[C:34]([CH3:35])=[C:33]([O:36][CH3:37])[C:32]([CH3:38])=[CH:31][N:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]2[CH:20]=[C:19]([CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[N:18]([CH2:28][C:29]3[C:34]([CH3:35])=[C:33]([O:36][CH3:37])[C:32]([CH3:38])=[CH:31][N:30]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of the crude octanoic acid (4-chloro-6-pyrrolidin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide (330 mg, 0.87 mmol), 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine (162 mg, 0.87 mmol) and K2CO3 (121 mg, 0.87 mmol) in dry DMF (1 mL) was heated to 45° C. overnight. After work-up (EtOAc) and evaporation, the residue was taken up in 6N methanolic HCl (1 mL), stirred at room temperature for 1 h, and neutralized to pH 7 with 2N NaOH. Extraction with EtOAc (10 mL×3), evaporation and purification by preparative TLC (MeOH/CH2Cl2 10:1) yielded 4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-6-pyrrolidin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (4.1 mg, yield 1.0%). HPLC Rt: 6.092 min. 1H-NMR (CDCl3): δ 8.09 (s, 1H), 6.31(s, 1H), 5.55(s, 2H), 4.85(s, 2H), 3.77 (s, 3H), 3.52(brs, 2H), 2.43 (m, 4H), 1.76–1.71 (m, 4H).

Workup

customAfter work-up (EtOAc) and evaporation
extractionExtraction
customwith EtOAc (10 mL×3), evaporation and purification by preparative TLC (MeOH/CH2Cl2 10:1)

Sources & evidence

ORD record: ord-2648099fe516446591fdaa4d0ca7708d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138402B2

Reaction notes

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