tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate → tert-butyl 3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxymethyl]pyrrolidine-1-carboxylate

HRID 2018768Notes

Reaction equation

HRID 2018768 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:14][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[CH3:15][n:16]1[n:31][cH:30][c:18]([NH:19][c:20]2[n:29][c:28]([c:23]3[c:22](Cl)[n:21]2)[nH:27][cH:26][c:24]3[Cl:25])[cH:17]1>>[CH3:15][n:16]1[n:31][cH:30][c:18]([NH:19][c:20]2[n:29][c:28]([c:23]3[c:22]([O:13][CH2:12][CH:11]4[CH2:14][N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH2:9][CH2:10]4)[n:21]2)[nH:27][cH:26][c:24]3[Cl:25])[cH:17]1

Participants

7

Reactant 2

HCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 866796474,5-dichloro-N-(1-methyl-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 123377533tert-butyl 3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxymethyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 23683543Potassium t-amylateReagentHCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 312751,4-DioxaneSolventHCID 117669-PhenylanthraceneInternal standard

Conditions

Temperature
100 °C

Sources & evidence

ORD record
ord-7436ba093c2e44439e5fa821709e0eab
Source dataset
39k HTE dataset from Pfizer
Original link
View source

Reaction notes

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