Phenyl chloroformate → Phenyl 3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenylcarbamate

HRID 1361672Notes

Reaction equation

HRID 1361672 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([CH3:23])[CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>C1COCC1>[CH3:23][C:4]1[CH:3]=[C:2]([NH:1][C:34](=[O:35])[O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:22]=[CH:21][C:5]=1[O:6][C:7]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=2)=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 469295424-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Product 1

HCID 58587930Phenyl 3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-(4-amino-2-methylphenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (200 mg, 0.65 mmol) in THF (4 mL) was added diisopropylethylamine (0.097 mL, 0.72 mmol) and phenyl chloroformate (102 mg, 0.65 mmol). The mixture was stirred for 3.5 hours at RT and used without purification.

Workup

  1. customused without purification

Sources & evidence

ORD record
ord-84fa883ac0a64121a7e780bb49bee632
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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