HuagongsheHuagongshe Chemistry Print Report · For research reference only
D-Alpha-aminobutyric acid → (R)-2-Chloro-5-methyl-7,8,9,10-tetrahydro-5H-pyrido[2,1-h]pteridin-6(6aH)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | D-Alpha-aminobutyric acid | HCID 439691 | — |
| Reactant | 2,4-Dichloro-5-nitropyrimidine | HCID 521266 | — |
| Reactant | Pipecolic acid, (+)- | HCID 736316 | — |
| Reactant | Methyl pipecolinate | HCID 3463753 | — |
| Reactant | methyl (2R)-2-aminobutanoate | HCID 13283514 | — |
| Product | (R)-2-Chloro-5-methyl-7,8,9,10-tetrahydro-5H-pyrido[2,1-h]pteridin-6(6aH)-one | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08445503B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-965d323307024e1eb5e36423f29c3658 |
| Source note | uspto-grants-2013_05 |