Tetrabutylammonium Fluoride → tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-methyl-butyl]carbamate

HRID 70767Notes

Reaction equation

HRID 70767 reaction equation
Br[C:2]1[C:3]([NH:9][CH:10]([CH:20]([CH3:22])[CH3:21])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.ClC1N=C(NCCNC(=O)OC(C)(C)C)C([C:41]#[C:42][CH:43]([O:47][CH2:48][CH3:49])[O:44][CH2:45][CH3:46])=CN=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].ClC1N=CC2C=C(C(OCC)OCC)N(CCNC(=O)OC(C)(C)C)C=2N=1>>[Cl:8][C:5]1[N:6]=[CH:7][C:2]2[CH:41]=[C:42]([CH:43]([O:47][CH2:48][CH3:49])[O:44][CH2:45][CH3:46])[N:9]([CH:10]([CH:20]([CH3:22])[CH3:21])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:3]=2[N:4]=1

Participants

5

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 86695593tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-3-methyl-butyl]carbamateHCID 86695595tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamateHCID 87428127Tert-butyl 2-(2-chloro-6-(diethoxymethyl)-7h-pyrrolo[2,3-d]pyrimidin-7-yl)ethylcarbamate

Product 1

HCID 89789738tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-methyl-butyl]carbamate

Procedure

tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-methyl-butyl]carbamate was synthesized by subjecting tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-3-methyl-butyl]carbamate to Sonogoshira conditions as described for tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamate followed by subsequent treatment with TBAF as described in the synthesis of tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamate. 1H NMR (600 MHz, DMSO-d6) δ ppm 1.11 (d, J=6.44 Hz, 3H) 1.18 (t, J=7.03 Hz, 6H) 1.21-1.26 (m, 12H) 2.88 (br. s., 1H) 3.43-3.78 (m, 6H) 3.97-4.08 (m, 1H) 5.61 (s, 1H) 6.65 (s, 1H) 6.71-6.78 (m, 1H) 8.87 (s, 1H). LCMS (ESI) 441 (M+H).

Sources & evidence

ORD record
ord-fd06854d16724d3ca4a1b7945beb6c67
Source dataset
uspto-grants-2014_09
Patent number
US08822683B2

Reaction notes

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