Pyridine → N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2,2-dimethylpropanamide

HRID 51479Notes

Reaction equation

HRID 51479 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][C:3]=1[O:24][CH3:25].N1[CH:31]=[CH:30][CH:29]=CC=1.C1(CC[C:40](Cl)=[O:41])C=CC=CC=1.Cl[CH2:44]Cl>>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:40](=[O:41])[C:30]([CH3:29])([CH3:31])[CH3:44])=[C:3]([O:24][CH3:25])[CH:4]=3)=[CH:9][N:10]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 64801Benzenepropanoyl chlorideHCID 227363445-(4-amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 22736334N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2,2-dimethylpropanamide

Procedure

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.147 mmol) was dissolved in dichloromethane (1.5 mL). Pyridine (1.5 mL) was added followed by 3-phenylpropanoyl chloride (37 mg, 0.221 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2,2-dimethylpropanamide (7 mg, 0.015 mmol). 1H NMR (CDCl3-d) δ 2.07 (m, 4H), 2.75 (m, 2H), 3.09 (m,2H), 3.65 (m, 2H), 3.88 (s, 3H), 4.13(m, 2H), 4.96 (m, 1H), 5.97 (bs, 2H), 6.93 (s, 1H), 7.05 (m, 2H), 7.26 (m, 5H), 7.70 (s, 1H), 8.24 (s, 1H), 8.46 (d, J=8.2 Hz, 1H). LC/MS: MH+=472.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in 1 ml DMSO
  3. additionmethanol (1 mL) was added
  4. customprecipitate was formed
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-ed97f2674adb4ea3afc14dc8845227bd
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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