Carbon tetrabromide → 4-(3-(Bromomethyl)phenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amine

HRID 577418Notes

Reaction equation

HRID 577418 reaction equation
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38]3[N:43]=[C:42]([S:44][C:45]4[CH:46]=[C:47](CO)[CH:48]=[CH:49][CH:50]=4)[CH:41]=[CH:40][N:39]=3)=[CH:33][CH:32]=2)[CH2:27][CH2:26]1>ClCCl>[Br:5][CH2:2][C:49]1[CH:50]=[C:45]([S:44][C:42]2[CH:41]=[CH:40][N:39]=[C:38]([NH:37][C:34]3[CH:33]=[CH:32][C:31]([N:28]4[CH2:27][CH2:26][O:25][CH2:30][CH2:29]4)=[CH:36][CH:35]=3)[N:43]=2)[CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 59491430HCID 59491430, compound

Product 1

HCID 594917074-(3-(Bromomethyl)phenylthio)-N-(4-morpholinophenyl)pyrimidin-2-amineYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of tetrabromomethane (370 mg, 1.12 mmol) and triphenylphosphine (293 mg, 1.12 mmol) in dichloromethane (10 mL), was added (3-(2-(4-morpholinophenylamino)pyrimidin-4-ylthio)phenyl)methanol (400 mg, 1.01 mmol) portionwise. After being stirred at room temperature for 1 hour, another batch of tetrabromomethane (370 mg, 1.12 mmol) and triphenylphosphine (293 mg, 1.12 mmol) was added to the mixture and the whole was stirred at room temperature for 1 hour. All of the volatiles were removed in vacuo, and the residue was flash chromatographed on silica gel using ethyl acetate:dichloromethane (0:100→10:90) as eluant to give the product (208 mg, 45%).

Workup

  1. stirringthe whole was stirred at room temperature for 1 hour
  2. customAll of the volatiles were removed in vacuo
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-00bbc207ae2c4a3db98e34cfaed7eaee
Source dataset
uspto-grants-2015_05
Patent number
US09040549B2

Reaction notes

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