Methanol → HCID 86729637, compound

HRID 2284909Notes

Reaction equation

HRID 2284909 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C.[Br:25][C:26]1[C:27](Cl)=[N:28][C:29]([Cl:32])=[N:30][CH:31]=1.CO>CN1C(=O)CCC1.C(Cl)Cl.O>[Br:25][C:26]1[C:27]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[N:28][C:29]([Cl:32])=[N:30][CH:31]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 86729637HCID 86729637, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl 2-aminophenylcarbamate (2 g, 9.6 mol) in NMP (15 mL), DIPEA (3.1 g, 24 mmol) and 5-bromo-2,4-dichloropyrimidine (2.78 g, 14.4 mmol) were added and heated to 120° C. for 1 h. TLC showed completion of starting material (TLC system: 5% methanol in DCM (Rf): 0.6). The reaction mixture was diluted with water (50 mL). The obtained solid was filtered, washed with water (35 mL) and dried to obtain tert-butyl 2-(5-bromo-2-chloropyrimidin-4-ylamino)phenylcarbamate as a pale yellow solid. Yield: (2.2 g, 62%). MS: m/z 399.1 (ES+, M+H).

Workup

  1. filtrationThe obtained solid was filtered
  2. washwashed with water (35 mL)
  3. customdried

Sources & evidence

ORD record
ord-557f7782c67b4a5baf3f5ddc336ae592
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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