Tetrahydro-2H-4-pyranyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate 5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine → HCID 22736305, compound

HRID 51543Notes

Reaction equation

HRID 51543 reaction equation
NC1C=CC(C2C3C(N)=NC=NC=3N(C3CCOCC3)C=2)=CC=1OC.[NH2:26][C:27]1[C:28]2[C:35]([C:36]3[CH:41]=[CH:40][C:39]([NH:42][C:43](=[O:51])[O:44][CH:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)=[C:38]([O:52][CH3:53])[CH:37]=3)=[CH:34][N:33]([CH:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[C:29]=2[N:30]=[CH:31][N:32]=1>N1C=CC=CC=1>[NH2:26][C:27]1[C:28]2[C:35]([C:36]3[CH:41]=[CH:40][C:39]([NH:42][C:43](=[O:51])[O:44][CH:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)=[C:38]([O:52][CH3:53])[CH:37]=3)=[CH:34][N:33]([CH:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[C:29]=2[N:30]=[CH:31][N:32]=1

Participants

3

Reactant 1

HCID 69921247Tetrahydro-2H-4-pyranyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate 5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 22736305HCID 22736305, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

Tetrahydro-2H-4-pyranyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate 5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (57 mg, 0.168 mmol) and 4-nitrophenyl tetrahydro-2H-4-pyranyl carbonate (90 mg, 0.336 mmol) was mixed in pyridine (1 mL). After stirring for 5 hours, another 90 mg of 4-nitrophenyl tetrahydro-2H-4-pyranyl carbonate was added and the reaction mixture was stirred for 2 days. The reaction mixture was heated at 70° C. for 2 hours. The solvent was removed and the residue was purified by preparative thin layer chromatography to give tetrahydro-2H-4-pyranyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (30 mg, 0.064 mmol). 1H NMR (CDCl3-d) δ 1.78 (m, 4H), 2.08 (m, 4H), 3.60 (m, 4H), 3.94 (s, 3H), 3.97 (m, 2H), 4.15 (m, 2H), 4.98 (m, 2H), 5.23 (s, 2H), 6.78 (s, 1H), 7.04 (s, 1H), 7.07 (d, J=8.3 Hz, 1H), 8.16 (bd, J=7.90 Hz, 1H), 8.33 (s, 1H). LC/MS MH+=468.

Workup

  1. stirringthe reaction mixture was stirred for 2 days
  2. customThe solvent was removed
  3. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-6920d893a500456bbe6cd2b8560cfc45
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

Loading…