Ammonia → HCID 178508692, compound

HRID 32540Notes

Reaction equation

HRID 32540 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OP(O)(O)=O.N1C(C(N)=O)=CN=C1.[NH2:28][C:29]1[C:34]([NH:35][C:36]([C:38]2[N:39]=[CH:40][N:41](COCC[Si](C)(C)C)[C:42]=2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=O)=[C:33]([NH2:57])[N:32]=[CH:31][N:30]=1.N>>[C:43]1([C:42]2[N:41]=[CH:40][NH:39][C:38]=2[C:36]2[NH:28][C:29]3[C:34]([N:35]=2)=[C:33]([NH2:57])[N:32]=[CH:31][N:30]=3)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 152917Imidazole-4-carboxamideHCID 69197507HCID 69197507, compound2×

Product 1

HCID 178508692HCID 178508692, compoundYield 6.1%

Conditions

Temperature
160 °C

Procedure

P2O5 (0.29 g) and H3PO4 (0.21 mL) were added to a mixture of N-(4,6-diaminopyrimidin-5-yl)-4-phenyl-1-{[2- trimethylsilyl)ethoxy]methyl}-1H-imidazole-5-carboxamide and N-(4,6-diaminopyrimidin-5-yl)-5-phenyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-4-carboxamide (Intermediate 36) (65 mg) and heated at 160° C. for 24 hours. After cooling to ambient temperature, ice was added and the reaction mixture adjusted to pH 5 with NH3 solution. The solvent was evaporated in vacuo to give a yellow oil. Purification by preparative RPHPLC (MeCN:water:TFA, 90:10:0.1) gave the title compound as a colourless solid (2.6 mg, 6%);

Workup

  1. temperatureAfter cooling to ambient temperature
  2. additionice was added
  3. customThe solvent was evaporated in vacuo
  4. customto give a yellow oil
  5. customPurification by preparative RPHPLC (MeCN:water:TFA, 90:10:0.1)

Sources & evidence

ORD record
ord-3fa6b9e5b0ec488da2772a8c08e9669e
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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