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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2093664Generated: October 26, 2026

D-Alpha-aminobutyric acid → (R)-2-Chloro-5-methyl-7,8,9,10-tetrahydro-5H-pyrido[2,1-h]pteridin-6(6aH)-one

https://huagongshe.com/reaction/2093664

Reaction equation

Participants

RoleNameHCIDCharge
ReactantD-Alpha-aminobutyric acidHCID 439691—
Reactant2,4-Dichloro-5-nitropyrimidineHCID 521266—
ReactantPipecolic acid, (+)-HCID 736316—
ReactantMethyl pipecolinateHCID 3463753—
Reactantmethyl (2R)-2-aminobutanoateHCID 13283514—
Product(R)-2-Chloro-5-methyl-7,8,9,10-tetrahydro-5H-pyrido[2,1-h]pteridin-6(6aH)-oneHCID 58405734—

Reaction Steps

Intermediate D was prepared in the same manner as intermediate B, using (R)-piperidine-2-carboxylic acid as the starting material instead of (R)-2-aminobutanoic acid. No reductive amination step, such as that used for the conversion of compound II to compound III, was required. Rather, methylpiperidine-2-carboxylate was reacted directly with 2,4-dichloro-5-nitropyrimidine in the same manner as is described for the conversion of compound III to intermediate A. 1H NMR (CDCl3) δ: 7.6 (s, 1H), 4.8 (m, 1H), 4.0 (m, 1H), 3.2 (s, 3H), 2.6 (m, 1H), 2.3 (m, 1H), 1.6 (m, 1H), 1.5 (m, 4H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445503B2
Source datasetuspto-grants-2013_05
ORD IDord-965d323307024e1eb5e36423f29c3658
Source noteuspto-grants-2013_05