2-(Dimethylamino)ethanol → [2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine

HRID 1910032Notes

Reaction equation

HRID 1910032 reaction equation
[Br:1][C:2]1[C:10]2[C:5]([NH:6][CH:7]=[N:8][C:9]=2[Cl:11])=[N:4][CH:3]=1.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178478408HCID 178478408, compound

Product 1

HCID 86663684[2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-4-chloro-1H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.860 mmol), 2-(dimethylamino)ethanol (230 mg, 2.58 mmol) and triphenylphosphine (451 mg, 1.721 mmol) in Tetrahydrofuran (THF) (10 mL) was added dropwise DEAD (0.272 mL, 1.721 mmol). The solution was allowed to stir at room temperature. After 2 hr the reaction was concentrated then loaded on to a 25 g Biotage SNAP column and eluted with 0 to 8% MeOH in DCM gradient over 30 minutes to give [2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine (175 mg, 67.0% yield) as a white solid. LC/MS (ES) m/z=303.1, 305.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.04 (s, 1H), 4.36 (t, J=6.19 Hz, 2H), 2.67 (t, J=6.19 Hz, 2H), 2.16 (s, 6H).

Workup

  1. concentrationAfter 2 hr the reaction was concentrated
  2. washeluted with 0 to 8% MeOH in DCM gradient over 30 minutes

Sources & evidence

ORD record
ord-6e57f09361bb455ea3bd19cabbcfe0c0
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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