Methylamine hydrochloride → HCID 58075784, compound

HRID 2370145Notes

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.Cl.[CH3:21][NH2:22]>>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][CH3:21])[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 6364545Methylamine hydrochloride

HCID 58075400HCID 58075400, compound

Product 1

HCID 58075784HCID 58075784, compoundYield 30.6%

Procedure

2,4-dichloro-8-(4-chlorophenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation K) (500 mg, 1.584 mmol) and methanamine hydrochloride (160 mg, 2.377 mmol) were combined and purified as per Preparation Ha to give 2-chloro-8-(4-chlorophenyl)-N-methyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (150 mg, 0.484 mmol, 30.5% yield). LC-MS (M+H)+=310.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.22-7.31 (2 H, m), 7.13 (2 H, d, J=8.55 Hz), 4.46-4.64 (1 H, m), 4.43 (1 H, br. s.), 3.97-4.14 (1 H, m), 3.91 (1 H, d, J=3.36 Hz), 3.09 (3 H, d, J=4.88 Hz).

Workup

custompurified as per Preparation Ha

Sources & evidence

ORD record: ord-c1503440e9de4e628a5941556327293e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710061B2

Reaction notes

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