Water → HCID 178475918, compound

HRID 1056847Notes

Reaction equation

HRID 1056847 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([OH:16])[C:6]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[S:9][C:7]=2[N:8]=1.C(N([CH2:22][CH3:23])CC)C.[OH2:24]>C(OC(=O)C)(=O)C>[OH:16][C:5]1[C:6]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[S:9][C:7]=2[N:8]=[C:3]([CH2:2][O:1][C:22](=[O:24])[CH3:23])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 178520003HCID 178520003, compound

Product 1

HCID 178475918HCID 178475918, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The 2-hydroxymethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-ol (4.5 g, 0.019 mol) in 10 ml of acetic anhydride was treated with triethylamine (3.8 g, 0.038 mol) at 0° C., and the mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water and the resulting solid was filtered, washed with water & hexanes, and dried to provide acetic acid 4-hydroxy-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylmethyl ester (4 g, 75%) as yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.74-1.90 (m, 4H), 2.21 (s, 3H), 2.70-2.80 (m, 2H), 2.95-3.02 (m, 2H), 5.07 (s, 2H), 10.52 (brs, 1H); LC-MS: [M+H]=279.1 m/z.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with water & hexanes
  3. customdried

Sources & evidence

ORD record
ord-63e8fea755744d9989ec5a501518d17e
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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