4-Methylmorpholine → HCID 178500477, compound

HRID 1108272Notes

Reaction equation

HRID 1108272 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:22])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([C:19]([OH:21])=O)[NH:17][CH:18]=3)[CH2:9][NH:8][C:6]=2[N:7]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[NH2:42][C@H:43]([C:50]([O:52][CH3:53])=[O:51])[CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([OH:22])[C:5]2[CH2:11][CH:10]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([C:19]([NH:42][C@H:43]([C:50]([O:52][CH3:53])=[O:51])[CH2:44][CH2:45][C:46]([O:48][CH3:49])=[O:47])=[O:21])[NH:17][CH:18]=3)[CH2:9][NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 12917568Dimethyl L-glutamate hydrochlorideHCID 1785088944-[2-(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pyrido[2,3-d]pyrimidin-6-yl)ethyl]-1H-pyrrole-2-carboxylic acid

Product 1

HCID 178500477HCID 178500477, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6yl)ethyl]pyrrole-2-carboxylic acid (152 mg, 0.5 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (98 mg, 0.55 mmol), and 4-methylmorpholine (0.066 mL, 0.6 mmol) in DMF (3 mL) was stirred at room temperature for 2 hours. Dimethyl L-glutamate hydrochloride (0.116 g, 0.55 mmol) and 4-methylmorpholine (0.066 mL, 0.6 mmol) were sequentially added and the mixture was stirred overnight at room temperature. The solvent was removed in vacuo, and the residue chromatographed using chloroform:methanol (9:1) to give dimethyl N-{4-[2-(amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrol-2-ylcarbonyl}-L-glutamate (152 mg, 66%) as a white solid, mp 151-153° C.: 1H N (CDCl3 /1 drop CD3OD) δ 10.20 (br s, 1H), 7.27 (s, 1H, J=7.9 Hz), 6.70 (s, 1H), 6.82 (s, 1H), 5.83 (br s, 2H), 5.38 (br s, 1H), 4.80 (m, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 3.42 (br d, 1H, J=10.1 Hz), 3.05 (m, 1H), 2.76 (dd, 1H, J=15.0, 4.4 Hz), 2.65 (m, 2H), 2.56 (m, 2H), 2.36 (m, 1H), 2.14 (m, 2H), 1.91 (m, 1H), 1.68 (m, 2H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed

Sources & evidence

ORD record
ord-1746a59bae5d4db0b49ac9aca24a5e59
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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