Dimethylamine → HCID 58075279, compound

HRID 2370146Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH3:20][NH:21][CH3:22]>>[Cl:1][C:2]1[N:3]=[C:4]([N:21]([CH3:22])[CH3:20])[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 58075400HCID 58075400, compound

Product 1

HCID 58075279HCID 58075279, compoundYield 78%

Procedure

2,4-dichloro-8-(4-chlorophenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation K) (500 mg, 1.584 mmol) and Dimethylamine (2.0 M in THF) (1.188 mL, 2.377 mmol) were combined an purified as per Preparation Ha to give 2-chloro-8-(4-chlorophenyl)-N,N-dimethyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (400 mg, 1.234 mmol, 78% yield) as a white solid. LC-MS (M+H)+=324.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.20-7.31 (2 H, m), 7.04-7.15 (2 H, m), 4.70-4.89 (2 H, m), 4.17 (1 H, dd, J=11.60, 5.49 Hz), 4.05 (1 H, t, J=5.49 Hz), 3.87 (1 H, dd, J=11.60, 5.49 Hz), 3.05-3.19 (6 H, m).

Workup

customan purified as per Preparation Ha

Sources & evidence

ORD record: ord-c55dabe38192453696f8138a1bdccc54
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710061B2

Reaction notes

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