Methanol → 6-Bromothieno[2,3-d]pyrimidine

HRID 1827695Notes

Reaction equation

HRID 1827695 reaction equation
C(N[C:8]1[N:9]=[C:10](NC(=O)C(C)(C)C)[C:11]2[C:16](CBr)=[C:15]([Br:19])[S:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.C1(NC2C=CC=CC=2)C=CC=CC=1.[H-].[Na+].CO>C1COCC1>[Br:19][C:15]1[S:14][C:12]2[N:13]=[CH:8][N:9]=[CH:10][C:11]=2[CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11487DiphenylamineHCID 24758Sodium hydride2×HCID 10625387HCID 10625387, compound

Product 1

HCID 122857306-Bromothieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-bis(pivaloylamino)-5-bromomethyl-6-bromothieno[2,3-d]pyrimidine prepared in Step 2 above (200 mg, 0.4 mmol), diphenylamine (1.3 g, 0.77 mmol) and NaH (50 mg, 2.1 mmol) in dry THF (10 mL) is stirred at room temperature for 2 days, the excess NaH is decomposed with MeOH (1 mL), the solvent is evaporated, and the residue is chromatographed on silica gel to obtain 2,4-bis(pivaloylamino)-5-N,N-diphenylaminomethyl)-6-bromothieno[2,3-d]pyrimidine.

Workup

  1. customthe solvent is evaporated
  2. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-98947d6412c24e39ba9cbc432f32cb30
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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