Triethylamine → HCID 86699680, compound

HRID 1487183Notes

Reaction equation

HRID 1487183 reaction equation
CS(O[CH2:6][C@@H:7]([C:9]1[C:10]([Cl:17])=[N:11][C:12]([Cl:16])=[N:13][C:14]=1Cl)[CH3:8])(=O)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>>[Cl:16][C:12]1[N:11]=[C:10]([Cl:17])[C:9]2[C@@H:7]([CH3:8])[CH2:6][N:27]([CH2:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[C:14]=2[N:13]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 86699681HCID 86699681, compound

Product 1

HCID 86699680HCID 86699680, compoundYield 74%

Procedure

(R)-2,4-dichloro-7-(4-methoxybenzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine was prepared from (R)-2-(2,4,6-trichloropyrimidin-5-yl)propyl methanesulfonate (60 mg, 0.188 mmol), (4-methoxyphenyl)methanamine (39 mg, 0.28 mmol) and triethyl amine (38 mg, 0.375 mmol), and isolated as a yellow (45 mg, yield 74%). 1H NMR (400 MHz, CDCl3) δ ppm 7.16-7.19 (d, 2H, J=8.8 Hz), 6.86-6.88 (d, 2H, J=8.4 Hz), 4.54 (s, 2H), 3.80 (s, 3H), 3.66-3.71 (t, 1H, J=6.0 Hz), 3.33-3.36 (m, 1H), 3.08-3.12 (dd, 1H, J=4.4 Hz, 10.0 Hz), 1.29-1.31 (d, 3H, J=6.8 Hz).

Workup

  1. customisolated as a yellow (45 mg, yield 74%)

Sources & evidence

ORD record
ord-fd28b6f4ac4a483db3c78f8ea6220821
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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