Methylamine hydrochloride → HCID 58075445, compound

HRID 2370147Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[N:14]=[C:15]([Cl:19])[N:16]=[C:17](Cl)[C:12]=3[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:21][NH2:22]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[N:14]=[C:15]([Cl:19])[N:16]=[C:17]([NH:22][CH3:21])[C:12]=3[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6364545Methylamine hydrochloride

HCID 58075521HCID 58075521, compound

Product 1

HCID 58075445HCID 58075445, compoundYield 42.6%

Procedure

8-(4-bromophenyl)-2,4-dichloro-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation L) (500 mg, 1.389 mmol) and methanamine hydrochloride (141 mg, 2.083 mmol) were combined and purified as per Preparation Ha to give 8-(4-bromophenyl)-2-chloro-N-methyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (210 mg, 0.592 mmol, 42.6% yield). LC-MS (M+H)+=356.0. 1H NMR (500 MHz, MeOD) δ ppm 7.46 (2 H, d, J=8.24 Hz), 7.13 (2 H, d, J=8.55 Hz), 4.43-4.71 (2 H, m), 4.09 (1 H, dd, J=11.44, 4.12 Hz), 3.92-4.03 (1 H, m), 3.86 (1 H, d, J=3.05 Hz), 3.00 (3 H, s).

Workup

custompurified as per Preparation Ha

Sources & evidence

ORD record: ord-72c8e036bf3c4e17993c06810edfc0c1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710061B2

Reaction notes

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