2,2-Dimethylpropyl carbonochloridate → HCID 54293747, compound

HRID 251493Notes

Reaction equation

HRID 251493 reaction equation
[CH2:1]([O:6][C:7](Cl)=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24]([NH2:26])=[N:23][CH:22]=[N:21][C:20]=3[N:19]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:18]=2)=[CH:13][C:12]=1[O:32][CH3:33]>N1C=CC=CC=1.ClCCl>[NH2:26][C:24]1[C:25]2[C:17]([C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:7](=[O:8])[O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])=[C:12]([O:32][CH3:33])[CH:13]=3)=[CH:18][N:19]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[C:20]=2[N:21]=[CH:22][N:23]=1

Participants

5

Reactant 2

HCID 33521852,2-Dimethylpropyl carbonochloridateHCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 54293747HCID 54293747, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Neopentylchloroformate (28 uL, 0.186 mmol) was added dropwise to a stirring solution of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (50 mg, 0.155 mmol) in pyridine (1 mL) and dichloromethane (1 mL) under nitrogen at 0° C. After 10 minutes, the ice water bath was removed and the resulting mixture was stirred for 4 hours. The solvent was evaporated and the residue was taken into ethyl acetate. The organic layer was washed, dried and evaporated. The solid was purified by preparative TLC using dichloromethane/methanol (95:5) as the mobile phase to give neopentyl N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate. 1H NMR (CDCl3) δ 1.00 (s 9H), 1.78 (m, 2H), 1.90 (m, 4H), 2.26 (m, 2H), 3.91 (s, 2H), 3.94 (s, 3H), 5.22 (m, 3H), 6.22 (s, 1H), 7.01 (s, 1H), 7.08 (d, J=8 Hz, 1H), 7.25 (s, 1H), 8.17 (br. d, 1H), 8.32 (s, 1H); LC/MS (MH+=438).

Workup

  1. customthe ice water bath was removed
  2. customThe solvent was evaporated
  3. washThe organic layer was washed
  4. customdried
  5. customevaporated
  6. customThe solid was purified by preparative TLC

Sources & evidence

ORD record
ord-ead8163023a741d58c0a116a5a8288bd
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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