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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 44808Generated: October 25, 2026

D-Proline → (R)-2-Chloro-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one

https://huagongshe.com/reaction/44808

Reaction equation

Participants

RoleNameHCIDCharge
ReactantD-ProlineHCID 8988—
ReactantMethyl DL-prolinateHCID 94239—
ReactantD-Alpha-aminobutyric acidHCID 439691—
Reactant2,4-Dichloro-5-nitropyrimidineHCID 521266—
Reactantmethyl (2R)-2-aminobutanoateHCID 13283514—
Product(R)-2-Chloro-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-oneHCID 58405567—

Reaction Steps

Intermediate E was prepared in the same manner as intermediate B, using (R)-pyrrolidine-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, methylpyrrolidine-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: 7.65 (s, 1H), 4.19 (m, 1H), 3.81 (m, 1H), 3.68 (m, 1H), 3.32 (s, 3H), 2.51 (m, 1H), 2.08 (m, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08541418B2
Source datasetuspto-grants-2013_09
ORD IDord-49b1b15dafd0400880cf940297720817
Source noteuspto-grants-2013_09